JP2018103469A - Recording material and recording sheet - Google Patents
Recording material and recording sheet Download PDFInfo
- Publication number
- JP2018103469A JP2018103469A JP2016252286A JP2016252286A JP2018103469A JP 2018103469 A JP2018103469 A JP 2018103469A JP 2016252286 A JP2016252286 A JP 2016252286A JP 2016252286 A JP2016252286 A JP 2016252286A JP 2018103469 A JP2018103469 A JP 2018103469A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- recording material
- methyl
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- BGLZECVIKIGPIF-UHFFFAOYSA-N 1-[2-(benzenesulfonamido)phenyl]-3-phenylurea Chemical compound C=1C=CC=C(NS(=O)(=O)C=2C=CC=CC=2)C=1NC(=O)NC1=CC=CC=C1 BGLZECVIKIGPIF-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 claims description 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 3
- 238000002441 X-ray diffraction Methods 0.000 claims description 2
- 238000010586 diagram Methods 0.000 claims 1
- 150000008331 benzenesulfonamides Chemical class 0.000 abstract 1
- -1 phenylurea compound Chemical class 0.000 description 78
- 239000010410 layer Substances 0.000 description 32
- 239000000975 dye Substances 0.000 description 30
- 238000012360 testing method Methods 0.000 description 25
- 239000006185 dispersion Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 14
- 229920002451 polyvinyl alcohol Polymers 0.000 description 14
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 14
- 239000004372 Polyvinyl alcohol Substances 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 238000011161 development Methods 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 12
- NSMMFSKPGXCMOE-UHFFFAOYSA-N 2-[2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=CC1=CC=CC=C1S(O)(=O)=O NSMMFSKPGXCMOE-UHFFFAOYSA-N 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 11
- 239000000945 filler Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003860 storage Methods 0.000 description 10
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 9
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 8
- 235000010350 erythorbic acid Nutrition 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- DINKXUCRJBUQAZ-UHFFFAOYSA-N tert-butyl 5-bromopyridine-3-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CN=CC(Br)=C1 DINKXUCRJBUQAZ-UHFFFAOYSA-N 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- UTNSTOOXQPHXJQ-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethoxy)phenyl]sulfonylphenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1S(=O)(=O)C1=CC=C(OCCO)C=C1 UTNSTOOXQPHXJQ-UHFFFAOYSA-N 0.000 description 3
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 3
- PRMDDINQJXOMDC-UHFFFAOYSA-N 4-[4,4-bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-cyclohexyl-5-methylphenol Chemical compound C=1C(C2CCCCC2)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C2CCCCC2)C=1)C)C(C(=CC=1O)C)=CC=1C1CCCCC1 PRMDDINQJXOMDC-UHFFFAOYSA-N 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C=*)(OC1)OC1C(C(O)=C1O)OC1=O Chemical compound CC(C=*)(OC1)OC1C(C(O)=C1O)OC1=O 0.000 description 3
- 239000004380 Cholic acid Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N Z-phenylurea Natural products NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 3
- 235000019416 cholic acid Nutrition 0.000 description 3
- 229960002471 cholic acid Drugs 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- AJXHXSKQHBJNPB-UHFFFAOYSA-N 1-methoxy-4-[2-[2-(4-methoxyphenoxy)ethoxy]ethoxy]benzene Chemical compound C1=CC(OC)=CC=C1OCCOCCOC1=CC=C(OC)C=C1 AJXHXSKQHBJNPB-UHFFFAOYSA-N 0.000 description 2
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 2
- LROZSPADHSXFJA-UHFFFAOYSA-N 2-(4-hydroxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1O LROZSPADHSXFJA-UHFFFAOYSA-N 0.000 description 2
- QKJAZPHKNWSXDF-UHFFFAOYSA-N 2-bromoquinoline Chemical compound C1=CC=CC2=NC(Br)=CC=C21 QKJAZPHKNWSXDF-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- FKZIDBGIZLBDDF-UHFFFAOYSA-N 4-(4-prop-2-enoxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(OCC=C)C=C1 FKZIDBGIZLBDDF-UHFFFAOYSA-N 0.000 description 2
- AJWUMVPXWNNESR-UHFFFAOYSA-N 6-n,6-n-diethyl-2-n-fluoro-3-methyloctane-2,6-diamine Chemical compound CCN(CC)C(CC)CCC(C)C(C)NF AJWUMVPXWNNESR-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- JXPQEGIVKMNZCZ-UHFFFAOYSA-N CNS(c1cccc2ccccc12)(=O)=O Chemical compound CNS(c1cccc2ccccc12)(=O)=O JXPQEGIVKMNZCZ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QWHCTYYBLDCYIT-UHFFFAOYSA-N bis[(4-chlorophenyl)methyl] oxalate Chemical compound C1=CC(Cl)=CC=C1COC(=O)C(=O)OCC1=CC=C(Cl)C=C1 QWHCTYYBLDCYIT-UHFFFAOYSA-N 0.000 description 2
- FPFZBTUMXCSRLU-UHFFFAOYSA-N bis[(4-methylphenyl)methyl] oxalate Chemical compound C1=CC(C)=CC=C1COC(=O)C(=O)OCC1=CC=C(C)C=C1 FPFZBTUMXCSRLU-UHFFFAOYSA-N 0.000 description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- JJXVDRYFBGDXOU-UHFFFAOYSA-N dimethyl 4-hydroxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(O)C=C1C(=O)OC JJXVDRYFBGDXOU-UHFFFAOYSA-N 0.000 description 2
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940012185 zinc palmitate Drugs 0.000 description 1
- XTUPUYCJWKHGSW-UHFFFAOYSA-L zinc;2-carboxy-4,6-bis(1-phenylethyl)phenolate Chemical compound [Zn+2].C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C([O-])=O)=CC=1C(C)C1=CC=CC=C1.C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C([O-])=O)=CC=1C(C)C1=CC=CC=C1 XTUPUYCJWKHGSW-UHFFFAOYSA-L 0.000 description 1
- IJQXGKBNDNQWAT-UHFFFAOYSA-L zinc;docosanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O IJQXGKBNDNQWAT-UHFFFAOYSA-L 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/3275—Fluoran compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
- B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Description
本発明は発色性染料と顕色剤との反応による発色を利用した記録材料、及びそれを用いた記録シートに関する。 The present invention relates to a recording material using color development caused by a reaction between a color-forming dye and a developer, and a recording sheet using the recording material.
発色性染料と顕色剤との反応による発色を利用した記録材料は、現像定着等の煩雑な処理を施すことなく比較的簡単な装置で短時間に記録できることから、ファクシミリ、プリンター等の出力記録のための感熱記録紙又は数枚を同時に複写する帳票のための感圧複写紙等に広く使用されている。これらの記録材料としては、速やかに発色し、未発色部分(以下「地肌」という)の白度が保持され、又発色した画像の堅牢性の高いものが要望されているが、長期保存安定性の面から、特に地肌及び画像の耐熱性に優れた記録材料が求められている。そのために、発色性染料、顕色剤、保存安定剤等の開発努力がなされ、発色の感度、地肌並びに画像の保存性などのバランスがさらに良いものが求められている。 Recording materials that utilize the color developed by the reaction between the color-forming dye and the developer can be recorded in a relatively simple device in a short time without complicated processing such as development and fixing. It is widely used for heat-sensitive recording paper for printing or pressure-sensitive copying paper for forms for copying several sheets simultaneously. These recording materials are required to develop colors quickly, maintain the whiteness of the uncolored areas (hereinafter referred to as “background”), and have high color fastness, but have long-term storage stability. In view of the above, there is a demand for a recording material that is particularly excellent in the heat resistance of the background and images. For this reason, efforts have been made to develop color developing dyes, color developers, storage stabilizers, and the like, and there is a demand for a better balance of color development sensitivity, background and image storage stability.
フェニルウレア系化合物を顕色剤として用いた記録材料が、特許文献1に記載されている。ここには、記録材料に含有され得る他の成分として、発色性染料、填料、分散剤のほか、他の顕色剤、画像安定剤、増感剤、酸化防止剤等としての公知化合物が挙げられている。
顕色剤として使用可能な有機酸は多数知られており、例えばアスコルビン酸又はその誘導体を顕色剤として用いることが特許文献2で提案されている。またアスコルビン酸又はその誘導体をその他の顕色剤と併用することも、特許文献3等に記載されている。さらに特許文献4には、アスコルビン酸又はその誘導体を、顕色剤分散液の保存安定性を向上させるための助剤として用いることが記載されている。
ステロール化合物は、可逆性感熱記録材料の成分や消色可能インク用の消色剤として用いることが知られている。例えば特許文献5には、コレステロールの脂肪酸エステルとコール酸等のステロイド骨格を有する脂肪酸とを含有する可逆性感熱記録材料が記載されている。また特許文献6には、ステロール化合物を含み加熱により消去可能なインク組成物が記載されている。
Patent Document 1 discloses a recording material using a phenylurea compound as a developer. Examples of other components that can be contained in the recording material include color developing dyes, fillers, dispersants, and other known compounds such as other color developers, image stabilizers, sensitizers, and antioxidants. It has been.
Many organic acids that can be used as a developer are known. For example, Patent Document 2 proposes to use ascorbic acid or a derivative thereof as a developer. In addition, the use of ascorbic acid or a derivative thereof in combination with another developer is described in Patent Document 3 and the like. Furthermore, Patent Document 4 describes that ascorbic acid or a derivative thereof is used as an auxiliary agent for improving the storage stability of the developer dispersion.
The sterol compound is known to be used as a component of a reversible thermosensitive recording material or a decoloring agent for a decolorable ink. For example, Patent Document 5 describes a reversible thermosensitive recording material containing a fatty acid ester of cholesterol and a fatty acid having a steroid skeleton such as cholic acid. Patent Document 6 describes an ink composition containing a sterol compound and erasable by heating.
本発明の目的は、発色性能、保存性等が良好な記録材料や記録シートを提供することにある。 An object of the present invention is to provide a recording material or a recording sheet having good color development performance, storage stability and the like.
本発明者は、N−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミドと併用するのに適した添加剤の検討を進める過程で、特定の化合物を添加剤として用いると、保存性が特に良好であることを見出して、本発明を完成するに至った。 In the process of studying an additive suitable for use in combination with N- (2- (3-phenylureido) phenyl) benzenesulfonamide, the present inventor uses a specific compound as an additive, so that the storage stability is improved. The present invention has been found to be particularly good, and the present invention has been completed.
すなわち、本発明は、以下の発明に関する。
(1)(A)発色性染料の少なくとも1種、
(B)下記式(I)
(式中、R1〜R3は、ハロゲン原子、ニトロ基、C1〜C6アルキル基、C1〜C6アルコキシ基、C2〜C6アルケニル基、C1〜C6ハロアルキル基、N(R4)2基(式中、R4は水素原子、フェニル基、ベンジル基、又はC1〜C6アルキル基を表す)、NHCOR5(式中、R5は、C1〜C6アルキル基を表す)、置換基を有してもよいフェニル基、又は置換基を有してもよいベンジル基を表し、n1及びn3は、それぞれ独立して、0〜5のいずれかの整数を表し、n2は、0〜4のいずれかの整数を表す)で表される化合物、
下記式(II)
(式中、R1〜R3は、式(I)におけるR1〜R3と同じものを表し、n2及びn3は、式(I)におけるn2及びn3と同じものを表し、n4は、0〜7のいずれかの整数を表す)で表される化合物、及び
下記式(III)
(式中、R1〜R3は、式(I)におけるR1〜R3と同じものを表し、n2、n3及びn4は、式(II)におけるn2、n3及びn4と同じものを表す)で表される化合物からなる群から選ばれる少なくとも1種、及び
(C)下記式(IV)
(式中、R11及びR12は、それぞれ独立して、水素原子、C1〜C6アルキル基、C2〜C6アルケニル基、又はC1〜C6アシル基(炭素数にカルボニル基の炭素を含む。)を表し、またR11とR12とが一緒になって5員環を形成してもよい。)で表される化合物、
下記式(V)
(式中、n11及びn12は、それぞれ独立して、1〜5のいずれかの整数を表す。)で表される化合物、
下記式(VI)
(式中、R8は水素原子、C1〜C6アルキル基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表し、R9及びR10はハロゲン原子、ニトロ基、C1〜C6アルキル基、C1〜C6アルコキシ基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表し、Arは置換基を有してもよいフェニル基又は置換基を有してもよい5〜6員ヘテロアリール基を表し、n9及びn10は独立して0〜4のいずれかの整数を表す。)で表される化合物、
下記式(VII)
(式中、R6及びR7は、それぞれ独立して、C1〜C6アルキル基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表す。)で表される化合物、及び
下記式(VIII)
(式中、n13〜n18は、それぞれ独立して、0又は1を表す。)
で表される化合物からなる群から選ばれる少なくとも1種、
を含有することを特徴とする記録材料。
(2)前記式(I)で表される化合物が、下記式(IX)
(3)前記式(IX)で表される化合物が、N−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミドである、(2)に記載の記録材料。
(4)N−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミドが、Cu−Kα線による粉末X線回折法における回折角(2θ±0.1度)が23.60度、20.80度、12.24度及び13.80度にピークを示すX線回折図により特徴づけられる結晶形のものである、(3)に記載の記録材料。
(5)発色性染料が、フルオラン系染料であることを特徴とする、(1)〜(4)のいずれかに記載の記録材料。
(6)支持体上に(1)〜(5)のいずれかに記載の記録材料から形成されてなる記録材料層を有することを特徴とする記録シート。
That is, the present invention relates to the following inventions.
(1) (A) at least one chromogenic dye,
(B) The following formula (I)
(Wherein R 1 to R 3 are a halogen atom, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 alkoxy group, a C 2 to C 6 alkenyl group, a C 1 to C 6 haloalkyl group, N (R 4 ) 2 groups (wherein R 4 represents a hydrogen atom, a phenyl group, a benzyl group, or a C 1 -C 6 alkyl group), NHCOR 5 (wherein R 5 is a C 1 -C 6 alkyl group) Represents a phenyl group that may have a substituent, or a benzyl group that may have a substituent, and n1 and n3 each independently represent an integer of 0 to 5 , N2 represents any integer of 0 to 4),
The following formula (II)
(Wherein R 1 to R 3 represent the same as R 1 to R 3 in formula (I), n2 and n3 represent the same as n2 and n3 in formula (I), and n4 represents 0 A compound represented by any one of -7, and the following formula (III)
(Wherein R 1 to R 3 represent the same as R 1 to R 3 in formula (I), and n2, n3, and n4 represent the same as n2, n3, and n4 in formula (II)). And at least one selected from the group consisting of compounds represented by formula (IV):
(Wherein R 11 and R 12 are each independently a hydrogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 1 -C 6 acyl group (the number of carbon And a compound represented by the following formula: R 11 and R 12 may be combined to form a 5-membered ring.
The following formula (V)
(Wherein, n11 and n12 each independently represents an integer of 1 to 5),
The following formula (VI)
(In the formula, R 8 represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 1 -C 6 haloalkyl group, and R 9 and R 10 represent a halogen atom, a nitro group, C 1 -C 6 alkyl group, C 1 -C 6 alkoxy group, C 2 -C 6 alkenyl group, or an C 1 -C 6 haloalkyl group, Ar is a phenyl group or a substituted group may have a substituent A 5- to 6-membered heteroaryl group which may have, n9 and n10 independently represent any integer of 0 to 4),
The following formula (VII)
(Wherein R 6 and R 7 each independently represent a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 1 -C 6 haloalkyl group), And the following formula (VIII)
(In the formula, n13 to n18 each independently represents 0 or 1.)
At least one selected from the group consisting of compounds represented by:
A recording material comprising:
(2) The compound represented by the formula (I) is represented by the following formula (IX)
(3) The recording material according to (2), wherein the compound represented by the formula (IX) is N- (2- (3-phenylureido) phenyl) benzenesulfonamide.
(4) N- (2- (3-phenylureido) phenyl) benzenesulfonamide has a diffraction angle (2θ ± 0.1 degrees) of 23.60 degrees in a powder X-ray diffraction method using Cu—Kα rays. The recording material according to (3), which is in a crystalline form characterized by an X-ray diffraction pattern showing peaks at 80 degrees, 12.24 degrees and 13.80 degrees.
(5) The recording material according to any one of (1) to (4), wherein the color-forming dye is a fluoran dye.
(6) A recording sheet comprising a recording material layer formed from the recording material according to any one of (1) to (5) on a support.
本発明によれば、発色性能及び保存性が良好な記録材料や記録シートを得ることができる。特に地肌耐熱性、発色画像の耐可塑剤性、耐油性及び耐熱性に優れた記録材料を得ることができる。 According to the present invention, it is possible to obtain a recording material or recording sheet having good color development performance and storage stability. In particular, it is possible to obtain a recording material having excellent background heat resistance, plasticizer resistance of color images, oil resistance, and heat resistance.
(記録材料)
本発明の記録材料は、発色性染料と顕色剤との反応による発色を利用した記録材料であって、少なくとも(A)発色性染料、(B)前記式(I)、(II)、及び(III)のいずれかで表される化合物、並びに(C)前記式(IV)、前記式(V)、前記式(VI)、前記式(VII)、及び前記式(VIII)のいずれかで表される化合物を含有するものである。
本発明の記録材料はどの様な用途にも使用でき、例えば、感熱記録材料又は感圧複写材料等に利用することができるが、特に感熱記録材料に利用することが好ましい。
(Recording material)
The recording material of the present invention is a recording material that utilizes color development by the reaction of a color-forming dye and a developer, and includes at least (A) a color-forming dye, (B) the formulas (I), (II), and A compound represented by any one of (III), and (C) any one of the formula (IV), the formula (V), the formula (VI), the formula (VII), and the formula (VIII). It contains the compound represented.
The recording material of the present invention can be used for any application. For example, it can be used for a heat-sensitive recording material or a pressure-sensitive copying material, but it is particularly preferably used for a heat-sensitive recording material.
((A)成分)
本発明の記録材料に使用される(A)成分である発色性染料としては、フルオラン系、フタリド系、ラクタム系、トリフェニルメタン系、フェノチアジン系、スピロピラン系等のロイコ染料を挙げることができるが、これらに限定されるものではなく、酸性物質である顕色剤と接触することにより発色する発色性染料であれば使用できる。また、これらの発色性染料は単独で使用し、その発色する色の記録材料を製造することは勿論であるが、それらの2種以上を混合使用することができる。例えば、赤色、青色、緑色の3原色の発色性染料又は黒発色性染料を混合使用して真に黒色に発色する記録材料を製造することができる。
このうち、フルオラン系発色性染料を好ましく挙げることができる。
((A) component)
Examples of the chromophoric dye that is the component (A) used in the recording material of the present invention include fluoran, phthalide, lactam, triphenylmethane, phenothiazine, and spiropyran leuco dyes. However, the present invention is not limited to these, and any chromogenic dye that develops color by contact with a developer that is an acidic substance can be used. In addition, these color-forming dyes are used alone to produce a recording material having the color to be developed, but two or more of them can be used in combination. For example, it is possible to produce a recording material that develops true black color by using a mixture of red, blue, and green primary color developing dyes or black coloring dyes.
Among these, a fluorane color-forming dye can be preferably mentioned.
発色性染料としては、例えば、3,3−ビス(p−ジメチルアミノフェニル)−フタリド、3,3−ビス(p−ジメチルアミノフェニル)−6−ジメチルアミノフタリド(別名クリスタルバイオレットラクトン)、3,3−ビス(p−ジメチルアミノフェニル)−6−ジエチルアミノフタリド、3,3−ビス(p−ジメチルアミノフェニル)−6−クロルフタリド、3,3−ビス(p−ジブチルアミノフェニル)−フタリド、3−シクロヘキシルアミノ−6−クロルフルオラン、3−ジメチルアミノ−5,7−ジメチルフルオラン、3−N−メチル−N−イソプロピルアミノ−6−メチル−7−アニリノフルオラン、3−N−メチル−N−イソブチルアミノ−6−メチル−7−アニリノフルオラン、3−N−メチル−N−イソアミルアミノ−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−7−クロロフルオラン、3−ジエチルアミノ−6,8−ジメチルフルオラン、3−ジエチルアミノ−7−メチルフルオラン、3−ジエチルアミノ−7,8−ベンズフルオラン、3−ジエチルアミノ−6−メチル−7−クロルフルオラン、3−ジブチルアミノ−6−メチル−7−ブロモフルオラン、3−(N−p−トリル−N−エチルアミノ)−6−メチル−7−アニリノフルオラン、3−ピロリジノ−6−メチルアミノ−7−アニリノフルオラン、2−{N−(3’−トリフルオルメチルフェニル)アミノ}−6−ジエチルアミノフルオラン、2−[3,6−ビス(ジエチルアミノ)−9−(o−クロルアニリノ)キサンチル]安息香酸ラクタム、3−ジエチルアミノ−6−メチル−7−(m−トリクロロメチルアニリノ)フルオラン、3−ジエチルアミノ−7−(o−クロルアニリノ)フルオラン、3−ジブチルアミノ−7−(o−クロルアニリノ)フルオラン、3−N−メチル−N−アミルアミノ−6−メチル−7−アニリノフルオラン、3−N−メチル−N−シクロヘキシルアミノ−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−メチル−7−(2’,4’−ジメチルアニリノ)フルオラン、3−(N,N−ジエチルアミノ)−5−メチル−7−(N,N−ジベンジルアミノ)フルオラン、3−(N,N−ジエチルアミノ)−7−(N,N−ジベンジルアミノ)フルオラン、3−(N−エチル−N−イソブチルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−プロピルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−メチル−N−プロピルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−イソペンチルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−トルイジノ)−6−メチル−7−アニリノ−フルオラン、3−ピロリジノ−6−メチル−7−アニリノフルオラン、3−ピペリジノ−6−メチル−7−アニリノフルオラン、3−ジメチルアミノ−7−(m−トリフルオロメチルアニリノ)フルオラン、3−ジペンチルアミノ−6−メチル−7−アニリノフルオラン、3−(N−エトキシプロピル−N−エチルアミノ)−6−メチル−7−アニリノフルオラン、3−ジブチルアミノ−7−(o−フルオロアニリノ)フルオラン、3−ジエチルアミノベンゾ[a]フルオラン、3−ジエチルアミノ−5−メチル−7−ベンジルアミノフルオラン、3−ジエチルアミノ−5−クロロフルオラン、3−ジエチルアミノ−6−(N,N’−ジベンジルアミノ)フルオラン、3,6−ジメトキシフルオラン、2,4−ジメチル−6−(4−ジメチルアミノフェニル)アミノフルオラン、3−ジエチルアミノ−7−(m−トリフルオロメチルアニリノ)フルオラン、3−ジエチルアミノ−6−メチル−7−オクチルアミノフルオラン、3−ジエチルアミノ−6−メチル−7−(m−トリルアミノ)フルオラン、3−ジエチルアミノ−6−メチル−7−(2,4−キシリルアミノ)フルオラン、3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオラン、3−ジフェニルアミノ−6−メチル−7−アニリノフルオラン、ベンゾイルロイコメチレンブルー、6’−クロロ−8’−メトキシ−ベンゾインドリノ−スピロピラン、6’−ブロモ−3’−メトキシ−ベンゾインドリノ−スピロピラン、3−(2’−ヒドロキシ−4’−ジメチルアミノフェニル)−3−(2’−メトキシ−5’−クロルフェニル)フタリド、3−(2’−ヒドロキシ−4’−ジメチルアミノフェニル)−3−(2’−メトキシ−5’−ニトロフェニル)フタリド、3−(2’−ヒドロキシ−4’−ジエチルアミノフェニル)−3−(2’−メトキシ−5’−メチルフェニル)フタリド、3−(2’−メトキシ−4’−ジメチルアミノフェニル)−3−(2’−ヒドロキシ−4’−クロル−5’−メチルフェニル)フタリド、3−モルホリノ−7−(N−プロピル−トリフルオロメチルアニリノ)フルオラン、3−ピロリジノ−7−トリフルオロメチルアニリノフルオラン、3−ジエチルアミノ−5−クロロ−7−(N−ベンジル−トリフルオロメチルアニリノ)フルオラン、3−ピロリジノ−7−(ジ−p−クロルフェニル)メチルアミノフルオラン、3−ジエチルアミノ−5−クロル−7−(α−フェニルエチルアミノ)フルオラン、3−(N−エチル−p−トルイジノ)−7−(α−フェニルエチルアミノ)フルオラン、3−ジエチルアミノ−7−(o−メトキシカルボニルフェニルアミノ)フルオラン、3−ジエチルアミノ−5−メチル−7−(α−フェニルエチルアミノ)フルオラン、3−ジエチルアミノ−7−ピペリジノフルオラン、2−クロロ−3−(N−メチルトルイジノ)−7−(p−n−ブチルアニリノ)フルオラン、3−(N−メチル−N−イソプロピルアミノ)−6−メチル−7−アニリノフルオラン、3−ジブチルアミノ−6−メチル−7−アニリノフルオラン、3−ジペンチルアミノ−6−メチル−7−アニリノフルオラン、3,6−ビス(ジメチルアミノ)フルオレンスピロ(9,3’)−6’−ジメチルアミノフタリド、3−(N−ベンジル−N−シクロヘキシルアミノ)−5,6−ベンゾ−7−α−ナフチルアミノ−4’−ブロモフルオラン、3−ジエチルアミノ−6−クロロ−7−アニリノフルオラン、3−N−エチル−N−(2−エトキシプロピル)アミノ−6−メチル−7−アニリノフルオラン、3−N−エチル−N−テトラヒドロフルフリルアミノ−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−メチル−7−メシチジノ−4’,5’−ベンゾフルオラン、3−(N−エチル−p−トルイジノ)−7−(メチルフェニルアミノ)フルオラン等が挙げられる。 Examples of color-forming dyes include 3,3-bis (p-dimethylaminophenyl) -phthalide, 3,3-bis (p-dimethylaminophenyl) -6-dimethylaminophthalide (also called crystal violet lactone), 3 , 3-bis (p-dimethylaminophenyl) -6-diethylaminophthalide, 3,3-bis (p-dimethylaminophenyl) -6-chlorophthalide, 3,3-bis (p-dibutylaminophenyl) -phthalide, 3-cyclohexylamino-6-chlorofluorane, 3-dimethylamino-5,7-dimethylfluorane, 3-N-methyl-N-isopropylamino-6-methyl-7-anilinofluorane, 3-N- Methyl-N-isobutylamino-6-methyl-7-anilinofluorane, 3-N-methyl-N-isoamylamino- -Methyl-7-anilinofluorane, 3-diethylamino-7-chlorofluorane, 3-diethylamino-6,8-dimethylfluorane, 3-diethylamino-7-methylfluorane, 3-diethylamino-7,8- Benzfluorane, 3-diethylamino-6-methyl-7-chlorofluorane, 3-dibutylamino-6-methyl-7-bromofluorane, 3- (Np-tolyl-N-ethylamino) -6 Methyl-7-anilinofluorane, 3-pyrrolidino-6-methylamino-7-anilinofluorane, 2- {N- (3′-trifluoromethylphenyl) amino} -6-diethylaminofluorane, 2- [3,6-bis (diethylamino) -9- (o-chloroanilino) xanthyl] lactam benzoate, 3-diethylamino-6-methyl -7- (m-trichloromethylanilino) fluorane, 3-diethylamino-7- (o-chloroanilino) fluorane, 3-dibutylamino-7- (o-chloroanilino) fluorane, 3-N-methyl-N-amylamino- 6-methyl-7-anilinofluorane, 3-N-methyl-N-cyclohexylamino-6-methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7-anilinofluorane, 3- Diethylamino-6-methyl-7- (2 ′, 4′-dimethylanilino) fluorane, 3- (N, N-diethylamino) -5-methyl-7- (N, N-dibenzylamino) fluorane, 3- (N, N-diethylamino) -7- (N, N-dibenzylamino) fluorane, 3- (N-ethyl-N-isobutylamino) -6-methyl -7-anilinofluorane, 3- (N-ethyl-N-propylamino) -6-methyl-7-anilinofluorane, 3- (N-methyl-N-propylamino) -6-methyl-7 -Anilinofluorane, 3- (N-ethyl-N-isopentylamino) -6-methyl-7-anilinofluorane, 3- (N-ethyl-N-toluidino) -6-methyl-7-anilino -Fluorane, 3-pyrrolidino-6-methyl-7-anilinofluorane, 3-piperidino-6-methyl-7-anilinofluorane, 3-dimethylamino-7- (m-trifluoromethylanilino) fluorane 3-dipentylamino-6-methyl-7-anilinofluorane, 3- (N-ethoxypropyl-N-ethylamino) -6-methyl-7-anilinofluorane, 3-dibutylamino 7- (o-fluoroanilino) fluorane, 3-diethylaminobenzo [a] fluorane, 3-diethylamino-5-methyl-7-benzylaminofluorane, 3-diethylamino-5-chlorofluorane, 3-diethylamino-6 -(N, N'-dibenzylamino) fluorane, 3,6-dimethoxyfluorane, 2,4-dimethyl-6- (4-dimethylaminophenyl) aminofluorane, 3-diethylamino-7- (m-tri Fluoromethylanilino) fluorane, 3-diethylamino-6-methyl-7-octylaminofluorane, 3-diethylamino-6-methyl-7- (m-tolylamino) fluorane, 3-diethylamino-6-methyl-7- ( 2,4-Xylylamino) fluorane, 3-diethylamino-7- (o-fluoro) Nilino) fluorane, 3-diphenylamino-6-methyl-7-anilinofluorane, benzoylleucomethylene blue, 6'-chloro-8'-methoxy-benzoindolino-spiropyran, 6'-bromo-3'-methoxy- Benzindolino-spiropyran, 3- (2′-hydroxy-4′-dimethylaminophenyl) -3- (2′-methoxy-5′-chlorophenyl) phthalide, 3- (2′-hydroxy-4′-dimethyl) Aminophenyl) -3- (2′-methoxy-5′-nitrophenyl) phthalide, 3- (2′-hydroxy-4′-diethylaminophenyl) -3- (2′-methoxy-5′-methylphenyl) phthalide , 3- (2′-methoxy-4′-dimethylaminophenyl) -3- (2′-hydroxy-4′-chloro-5′-methyl) Ruphenyl) phthalide, 3-morpholino-7- (N-propyl-trifluoromethylanilino) fluorane, 3-pyrrolidino-7-trifluoromethylanilinofluorane, 3-diethylamino-5-chloro-7- (N- Benzyl-trifluoromethylanilino) fluorane, 3-pyrrolidino-7- (di-p-chlorophenyl) methylaminofluorane, 3-diethylamino-5-chloro-7- (α-phenylethylamino) fluorane, 3- (N-ethyl-p-toluidino) -7- (α-phenylethylamino) fluorane, 3-diethylamino-7- (o-methoxycarbonylphenylamino) fluorane, 3-diethylamino-5-methyl-7- (α- Phenylethylamino) fluorane, 3-diethylamino-7-piperidinofluora 2-chloro-3- (N-methyltoluidino) -7- (pn-butylanilino) fluorane, 3- (N-methyl-N-isopropylamino) -6-methyl-7-anilinofluorane, 3- Dibutylamino-6-methyl-7-anilinofluorane, 3-dipentylamino-6-methyl-7-anilinofluorane, 3,6-bis (dimethylamino) fluorene spiro (9,3 ')-6' -Dimethylaminophthalide, 3- (N-benzyl-N-cyclohexylamino) -5,6-benzo-7-α-naphthylamino-4'-bromofluorane, 3-diethylamino-6-chloro-7-ani Linofluorane, 3-N-ethyl-N- (2-ethoxypropyl) amino-6-methyl-7-anilinofluorane, 3-N-ethyl-N-tetrahydrofluorine Ruamino-6-methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7-mesitidino-4 ′, 5′-benzofluorane, 3- (N-ethyl-p-toluidino) -7- ( Methylphenylamino) fluorane and the like.
これらの発色性染料の中では3−シクロヘキシルアミノ−6−クロロフルオラン、3−ジエチルアミノ−7−クロロフルオラン、3−ジエチルアミノ−6,8−ジメチルフルオラン、3−ジエチルアミノ−7−メチルフルオラン、3−ジエチルアミノ−7,8−ベンズフルオラン、3−ジエチルアミノ−6−メチル−7−クロロフルオラン、3−ジブチルアミノ−6−メチル−7−ブロモフルオラン、3−ジエチルアミノ−7−(o−クロロアニリノ)フルオラン、3−ジブチルアミノ−7−(o−クロロアニリノ)フルオラン、3−N−メチル−N−シクロヘキシルアミノ−6−メチル−7−アニリノフルオラン、3−(N,N−ジエチルアミノ)−5−メチル−7−(N,N−ジベンジルアミノ)フルオラン、3−(N,N−ジエチルアミノ)−7−(N,N−ジベンジルアミノ)フルオラン、3−(N−エチル−N−イソブチルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−メチル−N−プロピルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−イソペンチルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−トルイジノ)−6−メチル−7−アニリノ−フルオラン、3−(N−エトキシプロピル−N−エチルアミノ)−6−メチル−7−アニリノフルオラン、3−ジブチルアミノ−7−(o−フルオロアニリノ)フルオラン、3−ジエチルアミノ−7−(m−トリフルオロメチルアニリノ)フルオラン、3−ジエチルアミノ−6−メチル−7−オクチルアミノフルオラン、3−ジエチルアミノ−6−メチル−7−(m−トリルアミノ)フルオラン、3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオラン、3−ジフェニルアミノ−6−メチル−7−アニリノフルオラン、3−ジブチルアミノ−6−メチル−7−アニリノフルオラン、3−N−エチル−N−テトラヒドロフルフリルアミノ−6−メチル−7−アニリノフルオラン、3−(N−エチル−p−トルイジノ)−7−(メチルフェニルアミノ)フルオランを特に好ましく挙げることができる。 Among these chromogenic dyes, 3-cyclohexylamino-6-chlorofluorane, 3-diethylamino-7-chlorofluorane, 3-diethylamino-6,8-dimethylfluorane, 3-diethylamino-7-methylfluorane 3-diethylamino-7,8-benzfluorane, 3-diethylamino-6-methyl-7-chlorofluorane, 3-dibutylamino-6-methyl-7-bromofluorane, 3-diethylamino-7- (o -Chloroanilino) fluorane, 3-dibutylamino-7- (o-chloroanilino) fluorane, 3-N-methyl-N-cyclohexylamino-6-methyl-7-anilinofluorane, 3- (N, N-diethylamino) -5-methyl-7- (N, N-dibenzylamino) fluorane, 3- (N, N-diethyla) No) -7- (N, N-dibenzylamino) fluorane, 3- (N-ethyl-N-isobutylamino) -6-methyl-7-anilinofluorane, 3- (N-methyl-N-propyl) Amino) -6-methyl-7-anilinofluorane, 3- (N-ethyl-N-isopentylamino) -6-methyl-7-anilinofluorane, 3- (N-ethyl-N-toluidino) -6-methyl-7-anilino-fluorane, 3- (N-ethoxypropyl-N-ethylamino) -6-methyl-7-anilinofluorane, 3-dibutylamino-7- (o-fluoroanilino) Fluorane, 3-diethylamino-7- (m-trifluoromethylanilino) fluorane, 3-diethylamino-6-methyl-7-octylaminofluorane, 3-diethylamino-6-methyl 7- (m-Tolylamino) fluorane, 3-diethylamino-7- (o-fluoroanilino) fluorane, 3-diphenylamino-6-methyl-7-anilinofluorane, 3-dibutylamino-6-methyl-7 -Anilinofluorane, 3-N-ethyl-N-tetrahydrofurfurylamino-6-methyl-7-anilinofluorane, 3- (N-ethyl-p-toluidino) -7- (methylphenylamino) fluorane Can be mentioned particularly preferably.
また、近赤外吸収染料としては、3−[4−[4−(4−アニリノ)−アニリノ]アニリノ]−6−メチル−7−クロロフルオラン、3,3−ビス[2−(4−ジメチルアミノフェニル)−2−(4−メトキシフェニル)ビニル]−4,5,6,7−テトラクロロフタリド、3,6,6’−トリス(ジメチルアミノ)スピロ(フルオレン−9,3’−フタリド)等が挙げられる。 As the near infrared absorbing dye, 3- [4- [4- (4-anilino) -anilino] anilino] -6-methyl-7-chlorofluorane, 3,3-bis [2- (4- Dimethylaminophenyl) -2- (4-methoxyphenyl) vinyl] -4,5,6,7-tetrachlorophthalide, 3,6,6′-tris (dimethylamino) spiro (fluorene-9,3′- Phthalide) and the like.
((B)成分)
本発明の記録材料に使用される(B)成分は、顕色剤であって、式(I)
The component (B) used in the recording material of the present invention is a developer and has the formula (I)
式(II)
又は式(III)
のいずれかで表される化合物から選ばれる、少なくとも1種である。
ただし式(I)、(II)及び(III)中、R1〜R3としては、ハロゲン原子;ニトロ基;C1〜C6アルキル基;C1〜C6アルコキシ基;C2〜C6アルケニル基;C1〜C6ハロアルキル基;N(R4)2基(R4は水素原子、フェニル基、ベンジル基、又はC1〜C6アルキル基を表す);NHCOR5(R5はC1〜C6アルキル基を表す);置換基を有してもよいフェニル基;又は、置換基を有してもよいベンジル基を挙げることができる。
Or at least one selected from compounds represented by any of the above:
However, in the formulas (I), (II) and (III), R 1 to R 3 include a halogen atom; a nitro group; a C 1 to C 6 alkyl group; a C 1 to C 6 alkoxy group; and a C 2 to C 6. An alkenyl group; a C 1 -C 6 haloalkyl group; an N (R 4 ) 2 group (R 4 represents a hydrogen atom, a phenyl group, a benzyl group, or a C 1 -C 6 alkyl group); NHCOR 5 (R 5 is C 1 -C represents an alkyl group); an optionally substituted phenyl group; or, may be mentioned an optionally substituted benzyl group.
ここで、「ハロゲン原子」としては、弗素原子、塩素原子、臭素原子、沃素原子等を挙げることができる。
「C1〜C6アルキル基」としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、t−ブチル基、n−ペンチル基、イソペンチル基、ネオペンチル基、t−ペンチル基、n−ヘキシル基、イソヘキシル基、1−メチルペンチル基、2−メチルペンチル基等を挙げることができる。
「C1〜C6アルコキシ基」としては、メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基、n−ブトキシ基、sec−ブトキシ基、t−ブトキシ基等を挙げることができる。
「C2〜C6アルケニル基」としては、ビニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−メチル−2−プロペニル基、2−メチル−2−プロペニル基、1−ペンテニル基、2−ペンテニル基、3−ペンテニル基、4−ペンテニル基、1−メチル−2−ブテニル基、2−メチル−2−ブテニル基、1−ヘキセニル基、2−ヘキセニル基、3−ヘキセニル基、4−ヘキセニル基、5−ヘキセニル基等が挙げられる。
「C1〜C6ハロアルキル基」としては、クロロメチル基、ブロモメチル基、フルオロメチル基、トリフルオロメチル基、トリクロロメチル基、トリブロモメチル基、2,2,2−トリクロロエチル基、2,2、3,3,3−ペンタフルオロプロピル基又は1−クロロブチル基、6−フルオロへヘキシル基、6,6,6―トリフルオロへキシル基等が挙げられる。
「N(R4)2基」としては、メチルアミノ基、エチルアミノ基、n−プロピルアミノ基、n−ブチルアミノ基、n−へキシルアミノ基等のモノアルキルアミノ基;ジメチルアミノ基、ジエチルアミノ基、ジ−n−プロピルアミノ基、ジ−n−ブチルアミノ基等のジアルキルアミノ基;フェニルアミノ基、ジフェニルアミノ基、ベンジルアミノ基、ジベンジルアミノ基、メチルフェニルアミノ基等が挙げられる。
「NHCOR5」としては、NHCOCH3、NHCOC2H5、NHCOC5H11等が挙げられる。
Here, examples of the “halogen atom” include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of the “C 1 -C 6 alkyl group” include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group. Group, t-pentyl group, n-hexyl group, isohexyl group, 1-methylpentyl group, 2-methylpentyl group and the like.
Examples of the “C 1 -C 6 alkoxy group” include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, t-butoxy group and the like.
Examples of the “C 2 -C 6 alkenyl group” include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -Methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
Examples of the “C 1 -C 6 haloalkyl group” include chloromethyl group, bromomethyl group, fluoromethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trichloroethyl group, 2,2 3,3,3-pentafluoropropyl group or 1-chlorobutyl group, 6-fluorohexyl group, 6,6,6-trifluorohexyl group and the like.
“N (R 4 ) 2 group” includes monoalkylamino groups such as methylamino group, ethylamino group, n-propylamino group, n-butylamino group, n-hexylamino group; dimethylamino group, diethylamino group And dialkylamino groups such as di-n-propylamino group and di-n-butylamino group; phenylamino group, diphenylamino group, benzylamino group, dibenzylamino group, methylphenylamino group and the like.
Examples of “NHCOR 5 ” include NHCOCH 3 , NHCOC 2 H 5 , NHCOC 5 H 11 and the like.
また、「置換基を有してもよい」の置換基としては、水酸基;フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子;メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、t−ブチル基、n−ペンチル基、イソペンチル基、ネオペンチル基、t−ペンチル基、n−ヘキシル基、イソヘキシル基、1−メチルペンチル基、2−メチルペンチル基等のC1〜C6アルキル基;メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基、n−ブトキシ基、sec−ブトキシ基、t−ブトキシ基等のC1〜C6のアルコキシ基等を挙げることができる。 In addition, as the substituent of “may have a substituent”, a hydroxyl group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom; a methyl group, an ethyl group, an n-propyl group, an isopropyl group, n-butyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, t-pentyl group, n-hexyl group, isohexyl group, 1-methylpentyl group, 2-methylpentyl group C 1 -C 6 alkyl group such as a methoxy group, an ethoxy group, n- propoxy group, isopropoxy group, n- butoxy group, sec- butoxy group, an alkoxy group of C 1 -C 6, such as a t- butoxy group Can be mentioned.
好ましくは、R1〜R3としては、水素原子(n1〜n3が0の場合)又は直鎖状のC1〜C6アルキル基であり、さらに好ましくは、R1としては、水素原子又はメチル基であり、R2及びR3としては、水素原子である。
n1及びn3は、それぞれ独立して、0〜5のいずれかの整数を表し、n2は、0〜4のいずれかの整数を表す。n4は、1〜7のいずれかの整数を表す。
式(I)〜(III)で表される代表的な化合物としては、N−(3−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミド、N−(4−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミド、N−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミド、4−メチル−N−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミド等が挙げられる。これらの(B)成分の化合物は特許文献5により開示されている。
これらのうち、下記式(IX)
Preferably, R 1 to R 3 are a hydrogen atom (when n1 to n3 is 0) or a linear C 1 to C 6 alkyl group, and more preferably R 1 is a hydrogen atom or methyl And R 2 and R 3 are hydrogen atoms.
n1 and n3 each independently represents an integer of 0 to 5, and n2 represents an integer of 0 to 4. n4 represents the integer in any one of 1-7.
Representative compounds represented by formulas (I) to (III) include N- (3- (3-phenylureido) phenyl) benzenesulfonamide and N- (4- (3-phenylureido) phenyl) benzene. Sulfonamide, N- (2- (3-phenylureido) phenyl) benzenesulfonamide, 4-methyl-N- (2- (3-phenylureido) phenyl) benzenesulfonamide and the like can be mentioned. These compounds of component (B) are disclosed in Patent Document 5.
Of these, the following formula (IX)
で表される化合物が好ましく、中でもN−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミドが特に好ましい。 The compound represented by these is preferable, and N- (2- (3-phenylureido) phenyl) benzenesulfonamide is particularly preferable.
N−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミドは、2種の結晶形が存在することが本発明者らにより明らかにされている(国際特許出願番号PCT/JP2016/000836)。すなわち、Cu−Kα線による粉末X線回折法における回折角(2θ±0.1度)が、
5.80度、9.32度、24.52度及び23.40度にピークを示す結晶形I、及び
23.60度、20.80度、12.24度及び13.80度にピークを示す結晶形II
である。
(B)成分としては、結晶形I、II又はそれらの混合物であってもよいが、このうちの結晶形IIであるN−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミドを用いた場合に、保存安定性が特に向上するため、本発明においては、結晶形IIであるN−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミドを用いることが好ましい。
N- (2- (3-phenylureido) phenyl) benzenesulfonamide has been shown by the present inventors to exist in two crystal forms (International Patent Application No. PCT / JP2016 / 000836). That is, the diffraction angle (2θ ± 0.1 degrees) in the powder X-ray diffraction method using Cu—Kα rays is
Crystalline Form I showing peaks at 5.80 degrees, 9.32 degrees, 24.52 degrees and 23.40 degrees, and peaks at 23.60 degrees, 20.80 degrees, 12.24 degrees and 13.80 degrees Crystal form II shown
It is.
As the component (B), crystal form I, II or a mixture thereof may be used, but N- (2- (3-phenylureido) phenyl) benzenesulfonamide, which is crystal form II, is used. In this case, since storage stability is particularly improved, in the present invention, it is preferable to use N- (2- (3-phenylureido) phenyl) benzenesulfonamide, which is crystalline form II.
本発明の記録材料において、発色性染料に対する(B)成分の使用割合は、通常、発色性染料の1質量部に対し0.01〜10質量部、好ましくは0.5〜10質量部、好ましくは1.0〜5質量部、更に好ましくは1.5〜4.0質量部の割合である。
また、(B)成分は、感熱層を形成する固型分全体質量に対して、3〜35質量%の範囲で含まれているのが好ましく、更に好ましくは、10〜25質量%の範囲である。
また本発明の記録材料において、(B)成分に対する(C)成分の使用割合は、通常、(B)成分の1質量部に対し0.01〜5質量部、好ましくは0.1〜1質量部、さらに好ましくは0.3〜0.7質量部の割合である。
In the recording material of the present invention, the ratio of the component (B) to the color-forming dye is usually 0.01 to 10 parts by weight, preferably 0.5 to 10 parts by weight, preferably 1 part by weight of the color-forming dye. Is 1.0-5 mass parts, More preferably, it is a ratio of 1.5-4.0 mass parts.
Moreover, it is preferable that (B) component is contained in the range of 3-35 mass% with respect to the solid part whole mass which forms a thermosensitive layer, More preferably, it is in the range of 10-25 mass%. is there.
In the recording material of the present invention, the ratio of the component (C) to the component (B) is usually 0.01 to 5 parts by mass, preferably 0.1 to 1 part by mass with respect to 1 part by mass of the component (B). Parts, more preferably 0.3 to 0.7 parts by mass.
((C)成分)
本発明の記録材料に使用される添加剤である(C)成分は、
式(IV)
((C) component)
Component (C), which is an additive used in the recording material of the present invention,
Formula (IV)
で表される化合物、
式(V)
A compound represented by
Formula (V)
で表される化合物、
式(VI)
A compound represented by
Formula (VI)
で表される化合物、
式(VII)
A compound represented by
Formula (VII)
式(VIII)
で表される化合物である。
本発明において、(C)成分は、顕色剤である(B)成分と併用されることにより、発色性能、発色部及び未発色部の保存性等の顕色機能を改善する。(C)成分の範囲に包含される化合物としては、顕色機能改善の目的に応じて、複数種を併用してもよい。
It is a compound represented by these.
In the present invention, the component (C) is used in combination with the component (B), which is a developer, to improve the color development performance such as the color development performance, the storage stability of the color development part and the non-color development part. (C) As a compound included by the range of a component, you may use multiple types together according to the objective of a color development function improvement.
前記式(IV)で表される化合物において、R11及びR12は、それぞれ独立して、水素原子、C1〜6アルキル基、C2〜6アルケニル基、又はC1〜6アシル基を表し、またR11とR12とが一緒になって5員環を形成してもよい。
ここで、「C1〜C6アルキル基」及び「C2〜C6アルケニル基」としては、上記式(I)〜(III)における「C1〜C6アルキル基」及び「C2〜C6アルケニル基」と同じものを挙げることができる。
「C1〜C6アシル基」において、炭素数はカルボニル基の炭素を含む数である。「C1〜C6アシル基」としては、ホルミル基、アセチル基、プロピオニル基、ブチロイル基、ペンタノイル基等を挙げることができる。
前記のR11とR12とが一緒になって5員環を形成した化合物とは、アセタール誘導体又はケタール誘導体であり、具体的には式(X)
In the compound represented by the formula (IV), R 11 and R 12 each independently represent a hydrogen atom, C 1 ~ 6 alkyl group, C 2 ~ 6 alkenyl, or C 1 ~ 6 acyl group R 11 and R 12 may be combined to form a 5-membered ring.
Here, "C 1 -C 6 alkyl group" and as the "C 2 -C 6 alkenyl group", "C 1 -C 6 alkyl group" in the above formula (I) ~ (III) and "C 2 -C The same thing as " 6 alkenyl group" can be mentioned.
In the “C 1 -C 6 acyl group”, the carbon number is a number including carbon of the carbonyl group. Examples of the “C 1 -C 6 acyl group” include formyl group, acetyl group, propionyl group, butyroyl group, pentanoyl group and the like.
The compound in which R 11 and R 12 are combined to form a 5-membered ring is an acetal derivative or a ketal derivative, specifically, a compound represented by the formula (X)
(式中、R13及びR14はそれぞれ独立して、水素原子、又はC1〜C5アルキル基を表す。)により表される化合物である。
ここで、C1〜C5アルキル基としては、上記式(I)〜(III)における「C1〜C6アルキル基」のうち、C1〜C5に該当するものを挙げることができる。
また式(IV)で表される化合物には、立体異性体が存在する。これらの立体異性体のいずれを使用してもよく、またラセミ体、又は複数の化合物の混合物を使用してもよい。
以上のうち、R11及びR12が水素原子であることが好ましく、特に式(XI)
(Wherein R 13 and R 14 each independently represents a hydrogen atom or a C 1 -C 5 alkyl group).
Here, the C 1 -C 5 alkyl group, among the "C 1 -C 6 alkyl group" in the above formula (I) ~ (III), there may be mentioned those corresponding to the C 1 -C 5.
Moreover, a stereoisomer exists in the compound represented by Formula (IV). Any of these stereoisomers may be used, and a racemate or a mixture of a plurality of compounds may be used.
Of the above, R 11 and R 12 are preferably hydrogen atoms, and particularly represented by the formula (XI)
で表されるD−アラボアスコルビン酸(エリソルビン酸)が好ましい。
D-araboascorbic acid (erythorbic acid) represented by
前記式(V)で表される化合物において、n11及びn12は、それぞれ独立して、1〜5のいずれかの整数を表す。n11及びn12がいずれも1である化合物(化合物名:ビス[4−(2−ヒドロキシエトキシ)フェニル]スルホン)が好ましい。 In the compound represented by the formula (V), n11 and n12 each independently represents an integer of 1 to 5. A compound in which both n11 and n12 are 1 (compound name: bis [4- (2-hydroxyethoxy) phenyl] sulfone) is preferable.
前記式(VI)で表される化合物において、R8は水素原子、C1〜C6アルキル基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表し、R9及びR10はハロゲン原子、ニトロ基、C1〜C6アルキル基、C1〜C6アルコキシ基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表し、Arは置換基を有してもよいフェニル基又は置換基を有してもよい5〜6員ヘテロアリール基を表し、n9及びn10は独立して0〜4のいずれかの整数を表す。
ここで、R8〜R10の「C1〜C6アルキル基」、「C2〜C6アルケニル基」、「C1〜C6ハロアルキル基」、「ハロゲン原子」及び「C1〜C6アルコキシ基」は、上記式(I)〜(III)における「C1〜C6アルキル基」、「C2〜C6アルケニル基」、「C1〜C6ハロアルキル基」、「ハロゲン原子」及び「C1〜C6アルコキシ基」と同じものを挙げることができる。
Arが表す5〜6員ヘテロアリール基としては、ピロール−1−イル基、ピロール−2−イル基、ピロール−3−イル基、イミダゾール−1−イル基、イミダゾール−2−イル基、イミダゾール−4−イル基、フラン−2−イル基、フラン−3−イル基、2−チエニル基、3−チエニル基、ピラゾール−1−イル基、ピラゾール−3−イル基、ピラゾール−4−イル基、オキサゾール−2−イル基、オキサゾール−4−イル基、オキサゾール−5−イル基、イソオキサゾール−3−イル基、イソオキサゾール−4−イル基、イソオキサゾール−5−イル基、チアゾール−2−イル基、チアゾール−4−イル基、チアゾール−5−イル基、ピリジン−2−イル基、ピリジン−3−イル基、ピリジン−4−イル基等が挙げられる。
また、「置換基を有してもよい」の置換基としては、(B)成分に関して例示したものと同様の置換基を挙げることができる。
このうち、前記ヘテロアリール基としては、チアゾール−2−イル基であることが好ましく、特に、置換基を有しないチアゾール−2−イル基であることが好ましい。
R8は水素原子であることが好ましい。またn9及びn10はいずれも0であることが好ましい。
式(VI)で表される化合物としては、特に式(XII)
In the compound represented by the formula (VI), R 8 represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 1 -C 6 haloalkyl group, and R 9 and R 10 halogen atom represents a nitro group, C 1 -C 6 alkyl group, C 1 -C 6 alkoxy group, C 2 -C 6 alkenyl group, or a C 1 -C 6 haloalkyl group, Ar is substituted Or a phenyl group or a 5- to 6-membered heteroaryl group which may have a substituent, and n9 and n10 each independently represents an integer of 0 to 4.
Here, “C 1 -C 6 alkyl group”, “C 2 -C 6 alkenyl group”, “C 1 -C 6 haloalkyl group”, “halogen atom” and “C 1 -C 6 ” of R 8 to R 10. The “alkoxy group” means “C 1 -C 6 alkyl group”, “C 2 -C 6 alkenyl group”, “C 1 -C 6 haloalkyl group”, “halogen atom” in the above formulas (I) to (III) and It may include the same as the "C 1 -C 6 alkoxy group".
Examples of the 5- to 6-membered heteroaryl group represented by Ar include a pyrrol-1-yl group, a pyrrol-2-yl group, a pyrrol-3-yl group, an imidazol-1-yl group, an imidazol-2-yl group, and an imidazole- 4-yl group, furan-2-yl group, furan-3-yl group, 2-thienyl group, 3-thienyl group, pyrazol-1-yl group, pyrazol-3-yl group, pyrazol-4-yl group, Oxazol-2-yl group, oxazol-4-yl group, oxazol-5-yl group, isoxazol-3-yl group, isoxazol-4-yl group, isoxazol-5-yl group, thiazol-2-yl Group, thiazol-4-yl group, thiazol-5-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group and the like.
In addition, examples of the substituent “may have a substituent” include the same substituents as those exemplified for the component (B).
Among these, the heteroaryl group is preferably a thiazol-2-yl group, and particularly preferably a thiazol-2-yl group having no substituent.
R 8 is preferably a hydrogen atom. Moreover, it is preferable that both n9 and n10 are 0.
As the compound represented by formula (VI), in particular, formula (XII)
で表される化合物(化合物名:フタリルスルファチアゾール)が好ましい。
(Compound name: phthalyl sulfathiazole) is preferable.
前記式(VII)で表される化合物においては、R6及びR7は、それぞれ独立して、C1〜C6アルキル基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表す。
ここで、「C1〜C6アルキル基」、「C2〜C6アルケニル基」及び「C1〜C6ハロアルキル基」は、上記式(I)〜(III)における「C1〜C6アルキル基」、「C2〜C6アルケニル基」及び「C1〜C6ハロアルキル基」と同じものを挙げることができる。
R6及びR7は、C1〜C6アルキル基のいずれかであることが好ましく、共にメチル基であること(化合物名:2,6−ナフタレンジカルボン酸ジメチル)がより好ましい。
In the compound represented by the formula (VII), R 6 and R 7 each independently represents a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, or a C 1 to C 6 haloalkyl group. Represent.
Here, "C 1 -C 6 alkyl group", "C 2 -C 6 alkenyl group" and "C 1 -C 6 haloalkyl group", "C 1 -C in the above formula (I) ~ (III) 6 alkyl group "may include the same as the" C 2 -C 6 alkenyl group "and" C 1 -C 6 haloalkyl group ".
R 6 and R 7 are preferably any of C 1 to C 6 alkyl groups, and more preferably methyl groups (compound name: dimethyl 2,6-naphthalenedicarboxylate).
前記式(VIII)で表される化合物は、ステロイド骨格を有する脂肪酸である。n13〜n18は、それぞれ独立して、0又は1を表す。
これらの化合物には、水酸基の有無を異にする多数の化合物、また立体異性体が存在する。これらの化合物又は立体異性体のいずれを使用してもよく、またラセミ体や、複数の化合物の混合物を使用してもよい。
式(VIII)で表される化合物の代表的なものとしては、コラン酸、コ−ル酸、リトコ−ル酸、デオキシコ−ル酸、ヒオデオキシコ−ル酸、ケノデオキシコ−ル酸、ウルソデオキシコ−ル酸、デヒドロコ−ル酸、ホケコ−ル酸、ヒオコ−ル酸等が例示される。
以上のうち、特に式(XIII)
The compound represented by the formula (VIII) is a fatty acid having a steroid skeleton. n13 to n18 each independently represents 0 or 1.
These compounds include a large number of compounds having different hydroxyl groups and stereoisomers. Any of these compounds or stereoisomers may be used, and a racemate or a mixture of a plurality of compounds may be used.
Representative examples of the compound represented by the formula (VIII) include colanic acid, chololic acid, lithocholic acid, deoxycholic acid, hyodeoxycholic acid, chenodeoxycholic acid, ursodeoxychol. Examples thereof include acid, dehydrocholic acid, hoquetolic acid, and hyocholic acid.
Of the above, in particular, the formula (XIII)
で表されるコール酸が好ましい。
The cholic acid represented by these is preferable.
(記録材料の他の成分)
本発明の記録材料の中には、(A)、(B)、及び(C)の各成分の他に、その他の公知の顕色剤、増感剤、画像安定剤、填料、分散剤、酸化防止剤、粘着防止剤、消泡剤、光安定剤、蛍光増白剤等を必要に応じ1種又は2種以上含有させることができる。発色性染料以外の成分の使用量は、それぞれ、発色性染料1質量部に対して、通常0.1〜15質量部、好ましくは1〜10質量部の範囲である。
(Other components of recording material)
In the recording material of the present invention, in addition to the components (A), (B), and (C), other known color developers, sensitizers, image stabilizers, fillers, dispersants, One or more antioxidants, anti-tacking agents, antifoaming agents, light stabilizers, fluorescent brightening agents and the like can be contained as necessary. The amount of components other than the chromophoric dye is usually in the range of 0.1 to 15 parts by mass, preferably 1 to 10 parts by mass with respect to 1 part by mass of the chromogenic dye.
これらの薬剤は、発色層中に含有せしめてもよいが、多層構造からなる場合には、例えば、発色層の上部及び/又は下部にオーバーコート層やアンダーコート層を設けた場合、これらの層に含有することができる。さらに、酸化防止剤、光安定剤は必要に応じマイクロカプセルに内包する形で、これらの層に含有させることができる。 These agents may be contained in the color-developing layer. However, in the case of a multi-layer structure, for example, when an overcoat layer or an undercoat layer is provided above and / or below the color-developing layer, these layers are used. It can contain. Furthermore, an antioxidant and a light stabilizer can be contained in these layers in the form of being encapsulated in microcapsules, if necessary.
他の顕色剤としては具体的には例えば、次のものが例示できる。
ビスフェノールA、4,4’−sec−ブチリデンビスフェノール、4,4’−シクロヘキシリデンビスフェノール、2,2’−ビス(4−ヒドロキシフェニル)−3,3’−ジメチルブタン、2,2’−ジヒドロキシジフェニル、ペンタメチレン−ビス(4−ヒドロキシベンゾエート)、2,2−ジメチル−3,3−ジ(4−ヒドロキシフェニル)ペンタン、2,2−ビス(4−ヒドロキシフェニル)ヘキサン、2,2−ビス(4−ヒドロキシフェニル)プロパン、2,2−ビス(4−ヒドロキシフェニル)ブタン、2,2−ビス(4−ヒドロキシ−3−メチルフェニル)プロパン、4,4’−(1−フェニルエチリデン)ビスフェノール、4,4’−エチリデンビスフェノール、4−(4−ヒドロキシフェニル)−2−メチルフェノール、2,2’−ビス(4−ヒドロキシ−3−フェニル−フェニル)プロパン、4,4’−(1,3−フェニレンジイソプロピリデン)ビスフェノール、4,4’−(1,4−フェニレンジイソプロピリデン)ビスフェノール、2,2−ビス(4−ヒドロキシフェニル)酢酸ブチル等のビスフェノール化合物;4,4’−ジヒドロキシジフェニルチオエーテル、1,7−ジ(4−ヒドロキシフェニルチオ)−3,5−ジオキサヘプタン、2,2’−ビス(4−ヒドロキシフェニルチオ)ジエチルエーテル、4,4’−ジヒドロキシ−3,3’−ジメチルジフェニルチオエーテル等の含硫黄ビスフェノール化合物;4−ヒドロキシ安息香酸ベンジル、4−ヒドロキシ安息香酸エチル、4−ヒドロキシ安息香酸プロピル、4−ヒドロキシ安息香酸イソプロピル、4−ヒドロキシ安息香酸ブチル、4−ヒドロキシ安息香酸イソブチル、4−ヒドロキシ安息香酸4−クロロベンジル、4−ヒドロキシ安息香酸4−メチルベンジル、4−ヒドロキシ安息香酸ジフェニルメチル等の4−ヒドロキシ安息香酸エステル類;安息香酸亜鉛、4−ニトロ安息香酸亜鉛等の安息香酸金属塩、4−[2−(4−メトキシフェニルオキシ)エチルオキシ]サリチル酸等のサリチル酸類;サリチル酸亜鉛、ビス[4−(オクチルオキシカルボニルアミノ)−2−ヒドロキシ安息香酸]亜鉛等のサリチル酸金属塩;4,4’−ジヒドロキシジフェニルスルホン、2,4’−ジヒドロキシジフェニルスルホン、4−ヒドロキシ−4’−メチルジフェニルスルホン、4−ヒドロキシ−4’−イソプロポキシジフェニルスルホン、4−ヒドロキシ−4’−ブトキシジフェニルスルホン、4,4’−ジヒドロキシ−3,3’−ジアリルジフェニルスルホン、3,4−ジヒドロキシ−4’−メチルジフェニルスルホン、4,4’−ジヒドロキシ−3,3’,5,5’−テトラブロモジフェニルスルホン、4−アリルオキシ−4’−ヒドロキシジフェニルスルホン、2−(4−ヒドロキシフェニルスルホニル)フェノール、4,4’−スルホニルビス[2−(2−プロペニル)]フェノール、4−[{4−(プロポキシ)フェニル}スルホニル]フェノール、4−[{4−(アリロキシ)フェニル}スルホニル]フェノール、4−[{4−(ベンジロキシ)フェニル}スルホニル]フェノール、2,4−ビス(フェニルスルホニル)−5−メチル−フェノール等のヒドロキシスルホン類;4−フェニルスルホニルフェノキシ亜鉛、マグネシウム、アルミニウム、チタン等のヒドロキシスルホン類の多価金属塩類;4−ヒドロキシフタル酸ジメチル、4−ヒドロキシフタル酸ジシクロヘキシル、4−ヒドロキシフタル酸ジフェニル等の4−ヒドロキシフタル酸ジエステル類;2−ヒドロキシ−6−カルボキシナフタレン等のヒドロキシナフトエ酸のエステル類;トリブロモメチルフェニルスルホン等のトリハロメチルスルホン類;ヒドロキシアセトフェノン、p−フェニルフェノール、4−ヒドロキシフェニル酢酸ベンジル、p−ベンジルフェノール、ハイドロキノン−モノベンジルエーテル、2,4−ジヒドロキシ−2’−メトキシベンズアニリド、テトラシアノキノジメタン類、N−(2−ヒドロキシフェニル)−2−[(4−ヒドロキシフェニル)チオ]アセタミド、N−(4−ヒドロキシフェニル)−2−[(4−ヒドロキシフェニル)チオ]アセタミド、4−ヒドロキシベンゼンスルホンアニリド、4’−ヒドロキシ−4−メチルベンゼンスルホンアニリド、3−(3−フェニルウレイド)ベンゼンスルホンアニリド、オクタデシルリン酸、ドデシルリン酸;4,4’−ビス(N−p−トリルスルホニルアミノカルボニルアミノ)ジフェニルメタン、N−p−トリルスルホニル−N’−3−(p−トリルスルホニルオキシ)フェニルウレア、N−(p−トリルスルホニル)−N’−フェニルウレア、3,3’−ビス(p−トリルスルホニルアミノカルボニルアミノ)ジフェニルスルホン等の非フェノール系スルホニルウレア系化合物;4,4’−ビス[3−(4−メチル−3−フェノキシカルボニルアミノフェニル)ウレイド]ジフェニルスルホン、3−(3−フェニルウレイド)ベンゼンスルホンアミド、ビス[4−(n−オクチルオキシカルボニルアミノ)サリチル酸]亜鉛2水和物、4−[2−(4−メトキシフェノキシ)エトキシ]サリチル酸亜鉛、3,5−ビス(α−メチルベンジル)サリチル酸亜鉛等の非フェノール系化合物;又は下記式で表されるジフェニルスルホン架橋型化合物若しくはそれらの混合物等が挙げられる。
Specific examples of the other developer include the following.
Bisphenol A, 4,4′-sec-butylidene bisphenol, 4,4′-cyclohexylidene bisphenol, 2,2′-bis (4-hydroxyphenyl) -3,3′-dimethylbutane, 2,2′- Dihydroxydiphenyl, pentamethylene-bis (4-hydroxybenzoate), 2,2-dimethyl-3,3-di (4-hydroxyphenyl) pentane, 2,2-bis (4-hydroxyphenyl) hexane, 2,2- Bis (4-hydroxyphenyl) propane, 2,2-bis (4-hydroxyphenyl) butane, 2,2-bis (4-hydroxy-3-methylphenyl) propane, 4,4 ′-(1-phenylethylidene) Bisphenol, 4,4'-ethylidenebisphenol, 4- (4-hydroxyphenyl) -2-methylphenol, 2,2 ' Bis (4-hydroxy-3-phenyl-phenyl) propane, 4,4 ′-(1,3-phenylenediisopropylidene) bisphenol, 4,4 ′-(1,4-phenylenediisopropylidene) bisphenol, 2, Bisphenol compounds such as 2-bis (4-hydroxyphenyl) butyl acetate; 4,4′-dihydroxydiphenylthioether, 1,7-di (4-hydroxyphenylthio) -3,5-dioxaheptane, 2,2 ′ -Sulfur-containing bisphenol compounds such as bis (4-hydroxyphenylthio) diethyl ether and 4,4'-dihydroxy-3,3'-dimethyldiphenylthioether; benzyl 4-hydroxybenzoate, ethyl 4-hydroxybenzoate, 4- Propyl hydroxybenzoate, isopropyl 4-hydroxybenzoate, 4-hydro 4-hydroxybenzoic acid esters such as butyl xylbenzoate, isobutyl 4-hydroxybenzoate, 4-chlorobenzyl 4-hydroxybenzoate, 4-methylbenzyl 4-hydroxybenzoate, diphenylmethyl 4-hydroxybenzoate; Zinc acid, benzoic acid metal salts such as 4-nitrobenzoic acid zinc, salicylic acids such as 4- [2- (4-methoxyphenyloxy) ethyloxy] salicylic acid; zinc salicylate, bis [4- (octyloxycarbonylamino)- 2-hydroxybenzoic acid] salicylic acid metal salts such as zinc; 4,4′-dihydroxydiphenylsulfone, 2,4′-dihydroxydiphenylsulfone, 4-hydroxy-4′-methyldiphenylsulfone, 4-hydroxy-4′-iso Propoxydiphenylsulfone, 4-hydroxy-4 ' Butoxydiphenylsulfone, 4,4'-dihydroxy-3,3'-diallyldiphenylsulfone, 3,4-dihydroxy-4'-methyldiphenylsulfone, 4,4'-dihydroxy-3,3 ', 5,5'- Tetrabromodiphenylsulfone, 4-allyloxy-4′-hydroxydiphenylsulfone, 2- (4-hydroxyphenylsulfonyl) phenol, 4,4′-sulfonylbis [2- (2-propenyl)] phenol, 4-[{4 -(Propoxy) phenyl} sulfonyl] phenol, 4-[{4- (allyloxy) phenyl} sulfonyl] phenol, 4-[{4- (benzyloxy) phenyl} sulfonyl] phenol, 2,4-bis (phenylsulfonyl)- Hydroxysulfones such as 5-methyl-phenol; 4-phenylsulfonyl Polyvalent metal salts of hydroxysulfones such as enoxyzinc, magnesium, aluminum and titanium; 4-hydroxyphthalic acid diesters such as dimethyl 4-hydroxyphthalate, dicyclohexyl 4-hydroxyphthalate and diphenyl 4-hydroxyphthalate; 2 -Esters of hydroxynaphthoic acid such as hydroxy-6-carboxynaphthalene; Trihalomethyl sulfones such as tribromomethylphenylsulfone; Hydroxyacetophenone, p-phenylphenol, 4-hydroxyphenylacetic acid benzyl, p-benzylphenol, hydroquinone- Monobenzyl ether, 2,4-dihydroxy-2'-methoxybenzanilide, tetracyanoquinodimethanes, N- (2-hydroxyphenyl) -2-[(4-hydroxyphenyl) thio Acetamide, N- (4-hydroxyphenyl) -2-[(4-hydroxyphenyl) thio] acetamide, 4-hydroxybenzenesulfonanilide, 4'-hydroxy-4-methylbenzenesulfonanilide, 3- (3-phenyl Ureido) benzenesulfonanilide, octadecyl phosphoric acid, dodecyl phosphoric acid; 4,4′-bis (Np-tolylsulfonylaminocarbonylamino) diphenylmethane, Np-tolylsulfonyl-N′-3- (p-tolylsulfonyloxy) ) Non-phenolic sulfonylurea compounds such as phenylurea, N- (p-tolylsulfonyl) -N′-phenylurea, 3,3′-bis (p-tolylsulfonylaminocarbonylamino) diphenylsulfone; 4,4′- Bis [3- (4-methyl-3-phenoxycarbo Ruaminophenyl) ureido] diphenylsulfone, 3- (3-phenylureido) benzenesulfonamide, bis [4- (n-octyloxycarbonylamino) salicylic acid] zinc dihydrate, 4- [2- (4-methoxy) Non-phenolic compounds such as phenoxy) ethoxy] zinc salicylate and zinc 3,5-bis (α-methylbenzyl) salicylate; or diphenylsulfone cross-linked compounds represented by the following formulas or mixtures thereof.
本発明の記録材料において、発色性染料に対する(B)成分及びその他の顕色剤の合計量の使用割合は、発色性染料の1質量部に対し0.01〜10質量部、好ましくは0.5〜10質量部、好ましくは1.0〜5質量部、更に好ましくは1.5〜4.0質量部の割合である。
また、(B)成分及びその他の顕色剤の合計量は、感熱層を形成する固型分全体質量に対して、3〜35質量%の範囲で含まれているのが好ましく、更に好ましくは、10〜25質量%の範囲である。
また本発明の記録材料において、(B)成分及びその他の顕色剤の合計量に対する(C)成分の使用割合は、通常、(B)成分及びその他の顕色剤1質量部に対し0.01〜5質量部、好ましくは0.1〜2質量部、さらに好ましくは0.2〜1質量部の割合である。
In the recording material of the present invention, the ratio of the total amount of the component (B) and the other developer to the color-forming dye is 0.01 to 10 parts by weight, preferably 0. The ratio is 5 to 10 parts by mass, preferably 1.0 to 5 parts by mass, and more preferably 1.5 to 4.0 parts by mass.
Further, the total amount of the component (B) and the other developer is preferably included in the range of 3 to 35% by mass, more preferably based on the total mass of the solid component forming the heat-sensitive layer. 10 to 25% by mass.
In the recording material of the present invention, the ratio of the component (C) to the total amount of the component (B) and the other developer is usually 0. The ratio is 01 to 5 parts by mass, preferably 0.1 to 2 parts by mass, and more preferably 0.2 to 1 part by mass.
増感剤としては具体的には例えば、次のものが例示できる。
ステアリン酸アミド、ステアリン酸アニリド、又はパルチミン酸アミド等の高級脂肪酸アミド類;ベンズアミド、アセト酢酸アニリド、チオアセトアニリド、アクリル酸アミド、エチレンビスアミド、オルトトルエンスルホンアミド、パラトルエンスルホンアミド等のアミド類;フタル酸ジメチル、イソフタル酸ジベンジル、イソフタル酸ジメチル、テレフタル酸ジメチル、イソフタル酸ジエチル、イソフタル酸ジフェニル、テレフタル酸ジベンジル等のフタル酸ジエステル類;シュウ酸ジベンジル、シュウ酸ジ(4−メチルベンジル)、シュウ酸ジ(4−クロロベンジル)、シュウ酸ジベンジルとシュウ酸ジ(4−クロロベンジル)の等量混合物、シュウ酸ジ(4−クロロベンジル)とシュウ酸ジ(4−メチルベンジル)の等量混合物等のシュウ酸ジエステル類;2,2’−メチレンビス(4−メチル−6−t−ブチルフェノール)、4,4’−メチレン−ビス(2,6−ジ−t−ブチルフェノール)等のビス(t−ブチルフェノール)類;1,2−ビス(フェノキシ)エタン(略称EGPE)、1,2−ビス(4−メチルフェノキシ)エタン、1,2−ビス(3−メチルフェノキシ)エタン、1,2−ビス(フェノキシメチル)ベンゼン、1,2−ビス(4−メトキシフェニルチオ)エタン、1,2−ビス(4−メトキシフェノキシ)プロパン、1,3−フェノキシ−2−プロパノール、1,4−ジフェニルチオ−2−ブテン、1,4−ジフェニルチオブタン、1,4−ジフェノキシ−2−ブテン、1,5−ビス(4−メトキシフェノキシ)−3−オキサペンタン、1,3−ジベンゾイルオキシプロパン、ジベンゾイルオキシメタン、4,4’−エチレンジオキシ−ビス−安息香酸ジベンジルエステル、ビス〔2−(4−メトキシ−フェノキシ)エチル〕エーテル、2−ナフチルベンジルエーテル、1,3−ビス(2−ビニルオキシエトキシ)ベンゼン、1,4−ジエトキシナフタレン、1,4−ジベンジルオキシナフタレン、1,4−ジメトキシナフタレン、1,4−ビス(2−ビニルオキシエトキシ)ベンゼン、p−(2−ビニルオキシエトキシ)ビフェル、p−アリルオキシビフェニル、p−プロパギルオキシビフェニル、p−ベンジルオキシベンジルアルコール、4−(m−メチルフェノキシメチル)ビフェニル、(4−メチルフェニル)フェニルエーテル、N,N’−ジ(2−ナフチル)−1,4−フェニレンジアミン、ジフェニルアミン、カルバゾール、2,3−ジ−m−トリルブタン、4−ベンジルビフェニル、4,4’−ジメチルビフェニル;m−ターフェニル、p−ターフェニル等のターフェニル類;1,2−ビス(3,4−ジメチルフェニル)エタン、2,3,5,6−テトラメチル−4’−メチルジフェニルメタン、4−アセチルビフェニル、ジベンゾイルメタン、トリフェニルメタン、1−ヒドロキシ−2−ナフトエ酸フェニル、1−ヒドロキシ−2−ナフトエ酸メチル、N−オクタデシルカルバモイル−p−メトキシカルボニルベンゼン、p−ベンジルオキシ安息香酸ベンジル、β−ナフトエ酸フェニル、p−ニトロ安息香酸メチル、ジフェニルスルホン;炭酸ジフェニル、グアイアコールカーボネート、ジ−p−トリルカーボネート、フェニル−α−ナフチルカーボネート等の炭酸誘導体;p−(ベンジルオキシ)ベンジルアルコール、1,3−ジフェノキシ−2−プロパノール、1,1−ジフェニルプロパノール、1,1−ジフェニルエタノール、ベンズヒドロール、2−メチルベンズヒドロール、4−メチルベンズヒドロール、4,4′−ジメチルベンズヒドロール等の芳香族アルコール類;N−オクタデシルカルバモイルベンゼン、ジベンジルジスルフィド、ステアリン酸、アマイドAP−1(ステアリン酸アミドとパルミチン酸アミドの7:3混合物);ステアリン酸アルミニウム、ステアリン酸カルシウム、ステアリン酸亜鉛等のステアリン酸塩類;パルチミン酸亜鉛、ベヘン酸、ベヘン酸亜鉛、モンタン酸ワックス、ポリエチレンワックス等が挙げられる。
増感剤の種類によっては、記録シートの画像耐熱性等がやや劣る場合があるが、本発明の記録シートでは、式(I)で表される化合物をさらに併用することによってそのような問題を解決することもできる。
増感剤の使用量は、感熱記録層の全固型量のうち、1〜40質量%の範囲が好ましく、5〜25質量%の範囲がより好ましく、8〜20質量%の範囲がさらに好ましい。
Specific examples of the sensitizer include the following.
Higher fatty acid amides such as stearic acid amide, stearic acid anilide, or palmitic acid amide; Amides such as benzamide, acetoacetanilide, thioacetanilide, acrylic acid amide, ethylenebisamide, orthotoluenesulfonamide, paratoluenesulfonamide; Diesters such as dimethyl acid, dibenzyl isophthalate, dimethyl isophthalate, dimethyl terephthalate, diethyl isophthalate, diphenyl isophthalate, dibenzyl terephthalate; dibenzyl oxalate, di (4-methylbenzyl) oxalate, dioxalate (4-chlorobenzyl), an equivalent mixture of dibenzyl oxalate and di (4-chlorobenzyl) oxalate, an equivalent mixture of di (4-chlorobenzyl) oxalate and di (4-methylbenzyl) oxalate, etc. Oxalic acid diesters; bis (t-butylphenol) such as 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 4,4′-methylene-bis (2,6-di-tert-butylphenol) ); 1,2-bis (phenoxy) ethane (abbreviated EGPE), 1,2-bis (4-methylphenoxy) ethane, 1,2-bis (3-methylphenoxy) ethane, 1,2-bis (phenoxy) Methyl) benzene, 1,2-bis (4-methoxyphenylthio) ethane, 1,2-bis (4-methoxyphenoxy) propane, 1,3-phenoxy-2-propanol, 1,4-diphenylthio-2- Butene, 1,4-diphenylthiobutane, 1,4-diphenoxy-2-butene, 1,5-bis (4-methoxyphenoxy) -3-oxapentane, 1,3-diben Zoyloxypropane, dibenzoyloxymethane, 4,4′-ethylenedioxy-bis-benzoic acid dibenzyl ester, bis [2- (4-methoxy-phenoxy) ethyl] ether, 2-naphthylbenzyl ether, 1,3 -Bis (2-vinyloxyethoxy) benzene, 1,4-diethoxynaphthalene, 1,4-dibenzyloxynaphthalene, 1,4-dimethoxynaphthalene, 1,4-bis (2-vinyloxyethoxy) benzene, p -(2-vinyloxyethoxy) bifer, p-allyloxybiphenyl, p-propargyloxybiphenyl, p-benzyloxybenzyl alcohol, 4- (m-methylphenoxymethyl) biphenyl, (4-methylphenyl) phenyl ether, N, N′-di (2-naphthyl) -1,4-phenylenedi Min, diphenylamine, carbazole, 2,3-di-m-tolylbutane, 4-benzylbiphenyl, 4,4′-dimethylbiphenyl; terphenyls such as m-terphenyl and p-terphenyl; 1,2-bis ( 3,4-dimethylphenyl) ethane, 2,3,5,6-tetramethyl-4′-methyldiphenylmethane, 4-acetylbiphenyl, dibenzoylmethane, triphenylmethane, phenyl 1-hydroxy-2-naphthoate, 1 -Methyl hydroxy-2-naphthoate, N-octadecylcarbamoyl-p-methoxycarbonylbenzene, benzyl p-benzyloxybenzoate, phenyl β-naphthoate, methyl p-nitrobenzoate, diphenylsulfone; diphenyl carbonate, guaiacol carbonate, Di-p-tolyl carbonate, fluorine Carbonic acid derivatives such as nyl-α-naphthyl carbonate; p- (benzyloxy) benzyl alcohol, 1,3-diphenoxy-2-propanol, 1,1-diphenylpropanol, 1,1-diphenylethanol, benzhydrol, 2- Aromatic alcohols such as methylbenzhydrol, 4-methylbenzhydrol, 4,4'-dimethylbenzhydrol; N-octadecylcarbamoylbenzene, dibenzyldisulfide, stearic acid, amide AP-1 (with stearamide) 7: 3 mixture of palmitic acid amide); stearates such as aluminum stearate, calcium stearate, zinc stearate; zinc palmitate, behenic acid, zinc behenate, montanic acid wax, polyethylene wax and the like.
Depending on the type of the sensitizer, the image heat resistance and the like of the recording sheet may be slightly inferior. However, in the recording sheet of the present invention, such a problem is caused by further using a compound represented by the formula (I). It can also be solved.
The amount of the sensitizer used is preferably in the range of 1 to 40% by mass, more preferably in the range of 5 to 25% by mass, and still more preferably in the range of 8 to 20% by mass in the total solid amount of the heat-sensitive recording layer. .
画像安定剤としては、例えば、4−ベンジルオキシ−4’−(2−メチルグリシジルオキシ)−ジフェニルスルホン、4,4’−ジグリシジルオキシジフェニルスルホン等のエポキシ基含有ジフェニルスルホン類;1,4−ジグリシジルオキシベンゼン、4−[α−(ヒドロキシメチル)ベンジルオキシ]−4’−ヒドロキシジフェニルスルホン、2−プロパノール誘導体、サリチル酸誘導体、オキシナフトエ酸誘導体の金属塩(特に亜鉛塩)、(2,2−メチレンビス(4,6−ジ(t−ブチル)フェニル))ホスフェイトの金属塩、その他水不溶性の亜鉛化合物、2,2−ビス(4’−ヒドロキシ−3’,5’−ジブロモフェニル)プロパン、4,4’−スルホニルビス(2,6−ジブロモフェノール)、4,4’−ブチリデン(6−t−ブチル−3−メチルフェノール)、2,2’−メチレン−ビス(4−メチル−6−t−ブチルフェノール)、2,2’−メチレン−ビス(4−エチル−6−t−ブチルフェノール)、2,2’−ジ−t−ブチル−5,5’−ジメチル−4,4’−スルホニルジフェノール、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−シクロヘキシルフェニル)ブタン、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン等のヒンダードフェノール化合物、フェノールノボラック型化合物;エポキシレジン;UU(ケミプロ化成株式会社製)等を挙げることができる。
なお、画像安定剤は好ましくは常温で固体であり、特に好ましくは融点が60℃以上であり、水に溶けにくい化合物である。
画像安定剤は、(B)成分1質量部に対して、0.2〜0.5質量部の範囲で用いるのが好ましい。
また、画像安定剤は感熱記録層の全固型量のうち、1〜30質量%の範囲で使用するのが好ましく、5〜20質量%の範囲で使用するのがより好ましい。
Examples of the image stabilizer include epoxy group-containing diphenylsulfones such as 4-benzyloxy-4 ′-(2-methylglycidyloxy) -diphenylsulfone and 4,4′-diglycidyloxydiphenylsulfone; Diglycidyloxybenzene, 4- [α- (hydroxymethyl) benzyloxy] -4′-hydroxydiphenylsulfone, 2-propanol derivatives, salicylic acid derivatives, metal salts of oxynaphthoic acid derivatives (especially zinc salts), (2,2 -Metal salt of methylenebis (4,6-di (t-butyl) phenyl)) phosphate, other water-insoluble zinc compounds, 2,2-bis (4'-hydroxy-3 ', 5'-dibromophenyl) propane, 4,4′-sulfonylbis (2,6-dibromophenol), 4,4′-butylidene (6-tert-butyl-3) -Methylphenol), 2,2'-methylene-bis (4-methyl-6-tert-butylphenol), 2,2'-methylene-bis (4-ethyl-6-tert-butylphenol), 2,2'- Di-t-butyl-5,5′-dimethyl-4,4′-sulfonyldiphenol, 1,1,3-tris (2-methyl-4-hydroxy-5-cyclohexylphenyl) butane, 1,1,3 -A hindered phenol compound such as tris (2-methyl-4-hydroxy-5-t-butylphenyl) butane, a phenol novolac type compound; an epoxy resin; UU (manufactured by Chemipro Kasei Co., Ltd.), and the like.
The image stabilizer is preferably a solid at room temperature, particularly preferably a compound having a melting point of 60 ° C. or higher and hardly soluble in water.
The image stabilizer is preferably used in the range of 0.2 to 0.5 parts by mass with respect to 1 part by mass of component (B).
The image stabilizer is preferably used in the range of 1 to 30% by mass and more preferably in the range of 5 to 20% by mass in the total solid amount of the heat-sensitive recording layer.
填料としては、例えば、シリカ、クレー、カオリン、焼成カオリン、タルク、サテンホワイト、水酸化アルミニウム、炭酸カルシウム、炭酸マグネシウム、酸化亜鉛、酸化チタン、硫酸バリウム、珪酸マグネシウム、珪酸アルミニウム、プラスチックピグメント、珪藻土、タルク、水酸化アルミニウム等を挙げることができる。これらの中でも、焼成カオリン、炭酸カルシウムを好適に例示することができる。填料の使用割合は、発色性染料1質量部に対して0.1〜15質量部、好ましくは1〜10質量部である。また上記填料を混合して使用することも可能である。
また、填料は感熱記録層の全固型量のうち、50質量%以下で使用するのが好ましく、さらに30質量%以下で使用するのが好ましい。
Examples of fillers include silica, clay, kaolin, calcined kaolin, talc, satin white, aluminum hydroxide, calcium carbonate, magnesium carbonate, zinc oxide, titanium oxide, barium sulfate, magnesium silicate, aluminum silicate, plastic pigment, diatomaceous earth, Examples include talc and aluminum hydroxide. Among these, calcined kaolin and calcium carbonate can be preferably exemplified. The use ratio of the filler is 0.1 to 15 parts by mass, preferably 1 to 10 parts by mass with respect to 1 part by mass of the color forming dye. It is also possible to use a mixture of the above fillers.
The filler is preferably used in an amount of 50% by mass or less, more preferably 30% by mass or less, out of the total solid amount of the thermosensitive recording layer.
分散剤としては、例えば、ポリビニルアルコールや、アセトアセチル化ポリビニルアルコール、カルボキシ変性ポリビニルアルコール、スルホン酸変性ポリビニルアルコール、アマイド変性ポリビニルアルコール、ブチラール変性ポリビニルアルコールなどの各種のケン化度、重合度のポリビニルアルコール;メチルセルロース、カルボキシメチルセルロース、ヒドロキシエチルセルロース、エチルセルロース、アセチルセルロース、ヒドロキシメチルセルロース等のセルロース誘導体;ポリアクリル酸ソーダ;ポリアクリル酸エステル;ポリアクリルアミド;デンプン;スルホコハク酸ジオクチルナトリウム等のスルホコハク酸エステル類;ドデシルベンゼンスルホン酸ナトリウム;ラウリルアルコール硫酸エステルのナトリウム塩;脂肪酸塩;スチレン−無水マレイン酸共重合体;スチレン−ブタジエン共重合体;ポリ塩化ビニル;ポリ酢酸ビニル;ポリアクリル酸エステル;ポリビニルブチラール;ポリウレタン;ポリスチレン及びそれらの共重合体;ポリアミド樹脂;シリコーン樹脂;石油樹脂;テルペン樹脂;ケトン樹脂;クマロ樹脂等を挙げることができる。
分散剤は水、アルコール、ケトン、エステル、炭化水素等の溶剤に溶かして使用するほか、水又は他の溶媒中に乳化あるいはペースト状に分散させた状態で使用することも可能である。
分散剤は、感熱記録層の全固型分量のうち、5〜50質量%の範囲で使用するのが好ましく、10〜40質量%の範囲で使用するのがより好ましい。
Examples of the dispersant include polyvinyl alcohols having various saponification and polymerization degrees, such as polyvinyl alcohol, acetoacetylated polyvinyl alcohol, carboxy-modified polyvinyl alcohol, sulfonic acid-modified polyvinyl alcohol, amide-modified polyvinyl alcohol, and butyral-modified polyvinyl alcohol. Cellulose derivatives such as methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, ethylcellulose, acetylcellulose, and hydroxymethylcellulose; polyacrylic acid soda; polyacrylic acid ester; polyacrylamide; starch; sulfosuccinic acid esters such as dioctyl sodium sulfosuccinate; Sodium salt; sodium salt of lauryl alcohol sulfate; fat Styrene-maleic anhydride copolymer; styrene-butadiene copolymer; polyvinyl chloride; polyvinyl acetate; polyacrylate ester; polyvinyl butyral; polyurethane; polystyrene and copolymers thereof; polyamide resin; Examples include petroleum resins; terpene resins; ketone resins; coumaro resins.
The dispersant can be used by being dissolved in a solvent such as water, alcohol, ketone, ester, hydrocarbon or the like, or can be used in a state of being emulsified or pasted in water or another solvent.
The dispersant is preferably used in the range of 5 to 50% by mass and more preferably in the range of 10 to 40% by mass in the total solid content of the heat-sensitive recording layer.
酸化防止剤としては、例えば、2,2’−メチレンビス(4−メチル−6−t−ブチルフェノール)、2,2’−メチレンビス(4−エチル−6−t−ブチルフェノール)、4,4’−ブチリデンビス(3−メチル−6−t−ブチルフェノール)、4,4’−チオビス(2−t−ブチル−5−メチルフェノール)、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−t−ブチルフェニル)ブタン、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−シクロヘキシルフェニル)ブタン、4−{4−[1,1−ビス(4−ヒドロキシフェニル)エチル]−α,α−ジメチルベンジル}フェノール、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−シクロヘキシルフェニル)ブタン、2,2’−メチレンビス(6−tert−ブチル−4−メチルフェノール)、2,2’−メチレンビス(6−tert−ブチル−4−エチルフェノール)、4,4’−チオビス(6−tert−ブチル−3−メチルフェノール)、1,3,5−トリス[{4−(1,1−ジメチルエチル)−3−ヒドロキシ−2,6−ジメチルフェニル}メチル]−1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン、1,3,5−トリス[{3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシフェニル}メチル]−1,3,5−トリアジン−2,4,6(1H,3H,5H)−トリオン等を挙げることができる。 Examples of the antioxidant include 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-ethyl-6-tert-butylphenol), and 4,4′-butylidenebis. (3-methyl-6-tert-butylphenol), 4,4′-thiobis (2-tert-butyl-5-methylphenol), 1,1,3-tris (2-methyl-4-hydroxy-5-t) -Butylphenyl) butane, 1,1,3-tris (2-methyl-4-hydroxy-5-cyclohexylphenyl) butane, 4- {4- [1,1-bis (4-hydroxyphenyl) ethyl] -α , Α-dimethylbenzyl} phenol, 1,1,3-tris (2-methyl-4-hydroxy-5-cyclohexylphenyl) butane, 2,2′-methylenebis (6-tert-butyl) Til-4-methylphenol), 2,2′-methylenebis (6-tert-butyl-4-ethylphenol), 4,4′-thiobis (6-tert-butyl-3-methylphenol), 1,3, 5-Tris [{4- (1,1-dimethylethyl) -3-hydroxy-2,6-dimethylphenyl} methyl] -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -Trione, 1,3,5-tris [{3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl} methyl] -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione and the like.
粘着防止剤としては、例えば、ステアリン酸、ステアリン酸亜鉛、ステアリン酸カルシウム、カルナウバワックス、パラフィンワックス、エステルワックス等を挙げることができる。 Examples of the anti-sticking agent include stearic acid, zinc stearate, calcium stearate, carnauba wax, paraffin wax, ester wax and the like.
消泡剤としては、例えば、高級アルコール系、脂肪酸エステル系、オイル系、シリコーン系、ポリエーテル系、変性炭化水素系、パラフィン系等を挙げることができる。 Examples of the antifoaming agent include higher alcohols, fatty acid esters, oils, silicones, polyethers, modified hydrocarbons, and paraffins.
光安定剤としては、例えば、フェニルサリシレート、p−t−ブチルフェニルサリシレート、p−オクチルフェニルサリシレート等のサリチル酸系紫外線吸収剤;2,4−ジヒドロキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−ベンジルオキシベンゾフェノン、2−ヒドロキシ−4−オクチルオキシベンゾフェノン、2−ヒドロキシ−4−ドデシルオキシベンゾフェノン、2,2’−ジヒドロキシ−4−メトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジメトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−5−スルホベンゾフェノン、ビス(2−メトキシ−4−ヒドロキシ−5−ベンゾイルフェニル)メタン等のベンゾフェノン系紫外線吸収剤;2−(2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−t−ブチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−t−ブチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−t−ブチル−5’−メチルフェニル)−5−クロロベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−t−ブチルフェニル)−5−クロロベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−t−アミルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−tert−ブチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−(1'',1'',3'',3''−テトラメチルブチル)フェニル)ベンゾトリアゾール、2−[2’−ヒドロキシ−3’−(3'',4'',5'',6''−テトラヒドロフタルイミドメチル)−5’−メチルフェニル]ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−t−オクチルフェニル)ベンゾトリアゾール、2−[2’−ヒドロキシ−3’,5’−ビス(α,α−ジメチルベンジル)フェニル]−2H−ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−ドデシル−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−ウンデシル−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−トリデシル−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−テトラデシル−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−ペンタデシル−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−ヘキサデシル−5’−メチルフェニル)ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(2''−エチルヘキシル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(2''−エチルヘプチル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(2''−エチルオクチル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(2''−プロピルオクチル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(2''−プロピルヘプチル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(2''−プロピルヘキシル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(1''−エチルヘキシル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(1''−エチルヘプチル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(1’−エチルオクチル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(1''−プロピルオクチル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(1''−プロピルヘプチル)オキシフェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−4’−(1''−プロピルヘキシル)オキシフェニル]ベンゾトリアゾール、2,2’−メチレンビス[4−(1,1,3,3−テトラメチルブチル)−6−(2H−ベンゾトリアゾール−2−イル)]フェノール、ポリエチレングリコールとメチル−3−[3−t−ブチル−5−(2H−ベンゾトリアゾール−2−イル)−4−ヒドロキシフェニル]プロピオネートとの縮合物等のベンゾトリアゾール系紫外線吸収剤;2’−エチルヘキシル 2−シアノ−3,3−ジフェニルアクリレート、エチル 2−シアノ−3,3−ジフェニルアクリレート等のシアノアクリレート系紫外線吸収剤;ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケート、コハク酸−ビス(2,2,6,6−テトラメチル−4−ピペリジル)エステル、2−(3,5−ジ−t−ブチル)マロン酸−ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)エステル等のヒンダードアミン系紫外線吸収剤;1,8−ジヒドロキシ−2−アセチル−3−メチル−6−メトキシナフタレン等を挙げることができる。 Examples of the light stabilizer include salicylic acid UV absorbers such as phenyl salicylate, pt-butylphenyl salicylate, p-octylphenyl salicylate; 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2- Hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4-octyloxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4 Benzophenone ultraviolet absorbers such as' -dimethoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfobenzophenone, bis (2-methoxy-4-hydroxy-5-benzoylphenyl) methane; 2- (2'-hydroxy 5'-methylphenyl) benzotriazole, 2- (2'-hydroxy-5'-t-butylphenyl) benzotriazole, 2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) benzo Triazole, 2- (2′-hydroxy-3′-t-butyl-5′-methylphenyl) -5-chlorobenzotriazole, 2- (2′-hydroxy-3 ′, 5′-di-t-butylphenyl) ) -5-chlorobenzotriazole, 2- (2′-hydroxy-3 ′, 5′-di-t-amylphenyl) benzotriazole, 2- (2′-hydroxy-5′-tert-butylphenyl) benzotriazole 2- (2′-hydroxy-5 ′-(1 ″, 1 ″, 3 ″, 3 ″ -tetramethylbutyl) phenyl) benzotriazole, 2- [2′-hydroxy-3 '-(3 ″, 4 ″, 5 ″, 6 ″ -tetrahydrophthalimidomethyl) -5′-methylphenyl] benzotriazole, 2- (2′-hydroxy-5′-t-octylphenyl) benzo Triazole, 2- [2′-hydroxy-3 ′, 5′-bis (α, α-dimethylbenzyl) phenyl] -2H-benzotriazole, 2- (2′-hydroxy-3′-dodecyl-5′-methyl) Phenyl) benzotriazole, 2- (2′-hydroxy-3′-undecyl-5′-methylphenyl) benzotriazole, 2- (2′-hydroxy-3′-tridecyl-5′-methylphenyl) benzotriazole, 2 -(2'-hydroxy-3'-tetradecyl-5'-methylphenyl) benzotriazole, 2- (2'-hydroxy-3'-pentadecyl-5'- Tilphenyl) benzotriazole, 2- (2′-hydroxy-3′-hexadecyl-5′-methylphenyl) benzotriazole, 2- [2′-hydroxy-4 ′-(2 ″ -ethylhexyl) oxyphenyl] benzotriazole 2- [2′-hydroxy-4 ′-(2 ″ -ethylheptyl) oxyphenyl] benzotriazole, 2- [2′-hydroxy-4 ′-(2 ″ -ethyloctyl) oxyphenyl] benzotriazole 2- [2′-hydroxy-4 ′-(2 ″ -propyloctyl) oxyphenyl] benzotriazole, 2- [2′-hydroxy-4 ′-(2 ″ -propylheptyl) oxyphenyl] benzotriazole 2- [2′-hydroxy-4 ′-(2 ″ -propylhexyl) oxyphenyl] benzotriazole, 2 [2′-hydroxy-4 ′-(1 ″ -ethylhexyl) oxyphenyl] benzotriazole, 2- [2′-hydroxy-4 ′-(1 ″ -ethylheptyl) oxyphenyl] benzotriazole, 2- [ 2′-hydroxy-4 ′-(1′-ethyloctyl) oxyphenyl] benzotriazole, 2- [2′-hydroxy-4 ′-(1 ″ -propyloctyl) oxyphenyl] benzotriazole, 2- [2 '-Hydroxy-4'-(1 ″ -propylheptyl) oxyphenyl] benzotriazole, 2- [2′-hydroxy-4 ′-(1 ″ -propylhexyl) oxyphenyl] benzotriazole, 2,2 ′ -Methylenebis [4- (1,1,3,3-tetramethylbutyl) -6- (2H-benzotriazol-2-yl)] phenol, poly Benzotriazole ultraviolet absorbers such as condensates of ethylene glycol and methyl-3- [3-t-butyl-5- (2H-benzotriazol-2-yl) -4-hydroxyphenyl] propionate; 2′-ethylhexyl Cyanoacrylate-based UV absorbers such as 2-cyano-3,3-diphenyl acrylate and ethyl 2-cyano-3,3-diphenyl acrylate; bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate Succinic acid-bis (2,2,6,6-tetramethyl-4-piperidyl) ester, 2- (3,5-di-t-butyl) malonic acid-bis (1,2,2,6,6- Hindered amine ultraviolet absorbers such as pentamethyl-4-piperidyl) ester; 1,8-dihydroxy-2-acetyl-3-methyl-6-meth Naphthalene and the like.
蛍光増白剤としては、例えば、4,4’−ビス[2−アニリノ−4−(2−ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=二ナトリウム塩、4,4’−ビス[2−アニリノ−4−ビス(ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=二ナトリウム塩、4,4’−ビス[2−アニリノ−4−ビス(ヒドロキシプロピル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=二ナトリウム塩、4,4’−ビス[2−メトキシ−4−(2−ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=二ナトリウム塩、4,4’−ビス[2−メトキシ−4−(2−ヒドロキシプロピル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=二ナトリウム塩、4,4’−ビス[2−m−スルホアニリノ−4−ビス(ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=二ナトリウム塩、4−[2−p−スルホアニリノ−4−ビス(ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]−4’−[2−m−スルホアニリノ−4−ビス(ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=四ナトリウム塩、4,4’−ビス[2−p−スルホアニリノ−4−ビス(ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=四ナトリウム塩、4,4’−ビス[2−(2,5−ジスルホアニリノ)−4−フェノキシアミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=六ナトリウム塩、4,4’−ビス[2−(2,5−ジスルホアニリノ)−4−(p−メトキシカルボニルフェノキシ)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=六ナトリウム塩、4,4’−ビス[2−(p−スルホフェノキシ)−4−ビス(ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=六ナトリウム塩、4,4’−ビス[2−(2,5−ジスルホアニリノ)−4−ホルマリニルアミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=六ナトリウム塩、4,4’−ビス[2−(2,5−ジスルホアニリノ)−4−ビス(ヒドロキシエチル)アミノ−1,3,5−トリアジニル−6−アミノ]スチルベン−2,2’−ジスルホン酸=六ナトリウム塩等を挙げることができる。 Examples of the optical brightener include 4,4′-bis [2-anilino-4- (2-hydroxyethyl) amino-1,3,5-triazinyl-6-amino] stilbene-2,2′-disulfone. Acid = disodium salt, 4,4′-bis [2-anilino-4-bis (hydroxyethyl) amino-1,3,5-triazinyl-6-amino] stilbene-2,2′-disulfonic acid = disodium Salt, 4,4′-bis [2-anilino-4-bis (hydroxypropyl) amino-1,3,5-triazinyl-6-amino] stilbene-2,2′-disulfonic acid = disodium salt, 4′-bis [2-methoxy-4- (2-hydroxyethyl) amino-1,3,5-triazinyl-6-amino] stilbene-2,2′-disulfonic acid = disodium salt, 4,4′- Bi [2-Methoxy-4- (2-hydroxypropyl) amino-1,3,5-triazinyl-6-amino] stilbene-2,2′-disulfonic acid = disodium salt, 4,4′-bis [2- m-sulfoanilino-4-bis (hydroxyethyl) amino-1,3,5-triazinyl-6-amino] stilbene-2,2′-disulfonic acid = disodium salt, 4- [2-p-sulfoanilino-4- Bis (hydroxyethyl) amino-1,3,5-triazinyl-6-amino] -4 '-[2-m-sulfoanilino-4-bis (hydroxyethyl) amino-1,3,5-triazinyl-6-amino Stilbene-2,2′-disulfonic acid = tetrasodium salt, 4,4′-bis [2-p-sulfoanilino-4-bis (hydroxyethyl) amino-1,3,5-to Azinyl-6-amino] stilbene-2,2′-disulfonic acid = tetrasodium salt, 4,4′-bis [2- (2,5-disulfoanilino) -4-phenoxyamino-1,3,5-triazinyl- 6-Amino] stilbene-2,2′-disulfonic acid = hexasodium salt, 4,4′-bis [2- (2,5-disulfoanilino) -4- (p-methoxycarbonylphenoxy) amino-1,3 5-Triazinyl-6-amino] stilbene-2,2′-disulfonic acid = hexasodium salt, 4,4′-bis [2- (p-sulfophenoxy) -4-bis (hydroxyethyl) amino-1,3 , 5-Triazinyl-6-amino] stilbene-2,2′-disulfonic acid = hexasodium salt, 4,4′-bis [2- (2,5-disulfoanilino) -4-formalinylamino -1,3,5-triazinyl-6-amino] stilbene-2,2′-disulfonic acid = hexasodium salt, 4,4′-bis [2- (2,5-disulfoanilino) -4-bis (hydroxy And ethyl) amino-1,3,5-triazinyl-6-amino] stilbene-2,2′-disulfonic acid = hexasodium salt.
(記録シート)
本発明の記録シートは、前記のいずれかの記録材料から形成されてなる記録材料層を有する記録シートである。
(Recording sheet)
The recording sheet of the present invention is a recording sheet having a recording material layer formed from any of the recording materials described above.
本発明の記録シートにおいて、式(IV)〜式(VIII)のいずれかで表される化合物(C成分)は、発色性染料(A成分)と顕色剤(B成分)とを含有する発色層中に含有される。 In the recording sheet of the present invention, the compound (C component) represented by any one of formulas (IV) to (VIII) contains a color developing dye (component A) and a developer (component B). Contained in the layer.
本発明の記録シートとしては、感熱記録紙や感圧複写紙を挙げることができ、好ましくは感熱記録紙である。感熱記録紙に使用する場合には、既知の使用方法と同様に行えばよく、例えば、式(I)で表される化合物の微粒子をポリビニルアルコールやセルロース等の水溶性結合剤の水溶液中に分散させた懸濁液、及び発色性染料の微粒子及び顕色剤の微粒子のそれぞれを同様に分散させた懸濁液を混合して、紙等の支持体に塗布して乾燥することにより製造できる。 Examples of the recording sheet of the present invention include heat-sensitive recording paper and pressure-sensitive copying paper, preferably heat-sensitive recording paper. When used for heat-sensitive recording paper, it may be carried out in the same manner as in known methods. For example, fine particles of the compound represented by formula (I) are dispersed in an aqueous solution of a water-soluble binder such as polyvinyl alcohol or cellulose. It is possible to produce the suspension by mixing the suspension in which the fine particles of the color developing dye and the fine particles of the developer are similarly dispersed, applying the mixture to a support such as paper, and drying.
本発明の記録シートに使用する支持体は従来公知の紙、合成紙、古紙パルプ等の再生紙、フィルム、プラスチックフィルム、発泡プラスチックフィルム、不織布等を使用することができる。またこれらを組み合わせたものを支持体として使用することもできる。このうち紙を支持体とするものが好ましい。支持体の厚みには特に制限はないが、通常1〜500μm程度である。 As the support used in the recording sheet of the present invention, conventionally known paper, synthetic paper, recycled paper such as waste paper pulp, film, plastic film, foamed plastic film, non-woven fabric and the like can be used. Moreover, what combined these can also be used as a support body. Of these, those using paper as a support are preferred. Although there is no restriction | limiting in particular in the thickness of a support body, Usually, it is about 1-500 micrometers.
紙を支持体に用いる場合は、そのまま紙に発色性染料分散液、顕色剤分散液、増感剤分散液、及び填料分散液を含有する分散液を塗布してもよいが、予め、アンダーコート層分散液を塗布して乾燥させた後、前記分散液を塗布してもよい。好ましくは、アンダーコート層分散液を塗布した後、前記分散液を塗布した方が発色感度が良好である。
アンダーコート層分散液は、支持体の表面の平滑性を向上させるために用いるのであって、特に限定されるものではないが、填料、分散剤、水が含まれる方がよく、具体的には、填料としては焼成カオリン又は炭酸カルシウム、分散剤としてはポリビニルアルコールが好ましい。
When paper is used as a support, a dispersion containing a chromogenic dye dispersion, a developer dispersion, a sensitizer dispersion, and a filler dispersion may be applied to the paper as it is. After the coating layer dispersion is applied and dried, the dispersion may be applied. Preferably, the color development sensitivity is better when the undercoat layer dispersion is applied and then the dispersion is applied.
The undercoat layer dispersion is used for improving the smoothness of the surface of the support, and is not particularly limited, but preferably contains a filler, a dispersant, and water. The filler is preferably calcined kaolin or calcium carbonate, and the dispersant is preferably polyvinyl alcohol.
支持体上に記録材料層を形成させる場合には、染料分散液、顕色剤分散液、増感剤分散液、填料分散液を含有する分散液を支持体に塗布して乾燥させる方法が好ましく、他に分散液をスプレー等で噴霧して乾燥させる方法、分散液に一定時間浸漬して乾燥させる方法等が挙げられる。また、塗布する場合には、手塗り、サイズブレスコーター法、ロールコーター法、エアナイフコーター法、ブレンドコーター法、ブローコーター法、カーテンコーター法、コンマダイレクト法、グラビアダイレクト法、グラビアリバース法、リバース・ロールコーター法等が挙げられる。塗工量は、記録材料分散液の濃度にもよるが、乾燥後質量で通常0.1〜100g/m2、好ましくは1〜20g/m2の範囲である。 When forming a recording material layer on a support, a method of applying a dispersion containing a dye dispersion, a developer dispersion, a sensitizer dispersion, and a filler dispersion to the support and drying it is preferable. In addition, a method of spraying the dispersion with a spray or the like and drying, a method of immersing in the dispersion for a predetermined time and drying, etc. can be mentioned. When applying, hand coating, size breath coater method, roll coater method, air knife coater method, blend coater method, blow coater method, curtain coater method, comma direct method, gravure direct method, gravure reverse method, reverse Examples thereof include a roll coater method. Although the coating amount depends on the concentration of the recording material dispersion, it is usually in the range of 0.1 to 100 g / m 2 , preferably 1 to 20 g / m 2 in terms of the mass after drying.
以下、本発明の記録材料について実施例を挙げて詳細に説明するが、本発明は必ずしもこれだけに限定されるものではない。
なお、焼成カオリンとしてはAnsilex(登録商標)−93(BASF社製)を、また炭酸カルシウムとしてはBrilliant−15(白石カルシウム社製)を使用した。
Hereinafter, the recording material of the present invention will be described in detail with reference to examples, but the present invention is not necessarily limited thereto.
In addition, Ansilex (registered trademark) -93 (manufactured by BASF) was used as the calcined kaolin, and Brilliant-15 (manufactured by Shiraishi calcium) was used as the calcium carbonate.
感熱記録紙の作製及び試験
1)感熱記録紙の作製
[実施例1]
アンダーコート層用塗布液:
焼成カオリン 27.8部
ポリビニルアルコール10%水溶液 26.2部
水 71部
染料分散液(A液):
3−ジ−n−ブチルアミノ−6−メチル−7−アニリノフルオラン 16部
ポリビニルアルコール10%水溶液 84部
顕色剤分散液(B液):
N−(2−(3−フェニルウレイド)フェニル)ベンゼンスルホンアミド
II型結晶 16部
ポリビニルアルコール10%水溶液 84部
填料分散液(C液):
炭酸カルシウム 27.8部
ポリビニルアルコール10%水溶液 26.2部
水 71部
添加剤分散液(D液):
D−アラボアスコルビン酸 16部
ポリビニルアルコール10%水溶液 84部
(部は質量部)
アンダーコート層用塗布液、及びA〜D液の各組成の混合物をそれぞれサンドグラインダーで充分に磨砕して、A〜D液の各成分の分散液を調製した。
Production and test of thermal recording paper 1) Production of thermal recording paper [Example 1]
Undercoat layer coating solution:
Baked kaolin 27.8 parts 10% aqueous solution of polyvinyl alcohol 26.2 parts water 71 parts Dye dispersion (liquid A):
3-di-n-butylamino-6-methyl-7-anilinofluorane 16 parts polyvinyl alcohol 10% aqueous solution 84 parts developer dispersion (liquid B):
N- (2- (3-phenylureido) phenyl) benzenesulfonamide
Type II crystals 16 parts Polyvinyl alcohol 10% aqueous solution 84 parts Filler dispersion (liquid C):
Calcium carbonate 27.8 parts 10% aqueous solution of polyvinyl alcohol 26.2 parts Water 71 parts Additive dispersion (liquid D):
D-arabo ascorbic acid 16 parts 84% polyvinyl alcohol 10% aqueous solution 84 parts
(Part is part by mass)
The undercoat layer coating liquid and the mixture of each of the A to D liquid compositions were sufficiently ground with a sand grinder to prepare dispersions of the A to D liquid components.
白色紙上に、まずアンダーコート層用塗布液をワイヤーロッド(Webster社製、ワイヤーバーNO.12)を使用して塗布・乾燥してアンダーコート層を作製した。次に、A液1質量部、B液2質量部、C液4質量部、D液1質量部を混合して発色層用塗布液とした。アンダーコート層上に発色層用塗布液をワイヤーロッドを使用して塗布・乾燥した後、カレンダー掛け処理をして、感熱記録紙を作製した(発色層用塗布液は乾燥質量で約5.5g/m2)。 On the white paper, first, an undercoat layer coating solution was applied and dried using a wire rod (Webster, wire bar No. 12) to prepare an undercoat layer. Next, 1 part by mass of A liquid, 2 parts by mass of B liquid, 4 parts by mass of C liquid, and 1 part by mass of D liquid were mixed to prepare a coating solution for a color developing layer. After applying and drying the color layer coating solution on the undercoat layer using a wire rod, calendering was performed to prepare a thermal recording paper (the color layer coating solution was about 5.5 g in dry mass). / M 2 ).
[実施例2]
実施例1において、D−アラボアスコルビン酸に代えて、ビス[4−(2−ヒドロキシエトキシ)フェニル]スルホンを用いた以外は、実施例1と同様の方法で、感熱記録紙を作製した(発色層用塗布液は乾燥質量で約5.5g/m2)。
[Example 2]
In Example 1, a thermosensitive recording paper was produced in the same manner as in Example 1 except that bis [4- (2-hydroxyethoxy) phenyl] sulfone was used instead of D-araboascorbic acid ( The coating solution for the coloring layer is about 5.5 g / m 2 in terms of dry mass).
[実施例3]
実施例1において、D−アラボアスコルビン酸に代えて、フタリルスルファチアゾールを用いた以外は、実施例1と同様の方法で、感熱記録紙を作製した(発色層用塗布液は乾燥質量で約5.5g/m2)。
[Example 3]
In Example 1, a heat-sensitive recording paper was prepared in the same manner as in Example 1 except that phthalylsulfathiazole was used in place of D-araboascorbic acid (the color-forming layer coating solution was in dry mass). About 5.5 g / m 2 ).
[実施例4]
実施例1において、D−アラボアスコルビン酸に代えて、2,6−ナフタレンジカルボン酸ジメチルを用いた以外は、実施例1と同様の方法で、感熱記録紙を作製した(発色層用塗布液は乾燥質量で約5.5g/m2)。
[Example 4]
In Example 1, a heat-sensitive recording paper was prepared in the same manner as in Example 1 except that dimethyl 2,6-naphthalenedicarboxylate was used in place of D-araboascorbic acid (coloring layer coating solution) Is about 5.5 g / m 2 in dry mass).
[実施例5]
実施例1において、D−アラボアスコルビン酸に代えて、コール酸を用いた以外は、実施例1と同様の方法で、感熱記録紙を作製した(発色層用塗布液は乾燥質量で約5.5g/m2)。
[Example 5]
In Example 1, a heat-sensitive recording paper was produced in the same manner as in Example 1 except that cholic acid was used instead of D-araboascorbic acid (the color developing layer coating solution had a dry mass of about 5). .5 g / m 2 ).
[比較例1]
実施例1において、D−アラボアスコルビン酸に代えて、増感剤EGPEを用いた以外は、実施例1と同様の方法で、感熱記録紙を作製した(発色層用塗布液は乾燥質量で約5.5g/m2)。
[Comparative Example 1]
In Example 1, a heat-sensitive recording paper was prepared in the same manner as in Example 1 except that sensitizer EGPE was used instead of D-araboascorbic acid (the color-forming layer coating solution was in dry mass). About 5.5 g / m 2 ).
2)地肌の保存性試験
各評価サンプルに関して、試験前後の各試験紙について以下の各条件で保存性試験を行った。その結果を表1に示した。
2) Preservation test of the background For each evaluation sample, a preservability test was performed on each test paper before and after the test under the following conditions. The results are shown in Table 1.
[試験前]
各感熱記録紙の一部を切り取り、地肌の光学濃度を分光測色計(SpectroeyeLT、X-rite社製)で測定した。
[Before test]
A part of each thermal recording paper was cut out, and the optical density of the background was measured with a spectrocolorimeter (Spectroeye LT, manufactured by X-rite).
[耐熱性試験]
各感熱記録紙の一部を切り取り、恒温器(商品名:DK−400、YAMATO製)中で90℃、100℃の各温度で24時間保持した。保持した後の地肌の光学濃度を分光測色計(SpectroeyeLT、X-rite社製)で測定した。
[Heat resistance test]
A part of each thermal recording paper was cut out and kept at 90 ° C. and 100 ° C. for 24 hours in a thermostatic chamber (trade name: DK-400, manufactured by YAMATO). The optical density of the background after being held was measured with a spectrocolorimeter (Spectroeye LT, manufactured by X-rite).
[耐湿熱性試験]
各感熱記録紙の一部を切り取り、低温恒温恒湿器(商品名:THN050FA、ADVANTEC製)中で温度40℃、湿度90%の条件で24時間保持した。試験後の光学濃度を分光測色計(SpectroeyeLT、X-rite社製)で測定した。
[Moisture and heat resistance test]
A part of each thermal recording paper was cut out and kept in a low-temperature thermo-hygrostat (trade name: THN050FA, manufactured by ADVANTEC) at a temperature of 40 ° C. and a humidity of 90% for 24 hours. The optical density after the test was measured with a spectrocolorimeter (Spectroeye LT, manufactured by X-rite).
表1の結果から、本発明の記録シートは地肌の耐熱性と耐湿熱性に優れていることが判明した。 From the results in Table 1, it was found that the recording sheet of the present invention was excellent in the heat resistance and heat and moisture resistance of the background.
3)画像の保存性試験
各評価サンプルに関して、発色させた画像について以下の各条件で保存性試験を行った。その結果を表2に示した。
3) Image storability test With respect to each evaluation sample, a storability test was performed on the colored image under the following conditions. The results are shown in Table 2.
[試験前]
各感熱記録紙の一部を切り取り、感熱紙発色試験装置(商品名: TH−PMH型、大倉電機製)を使用し、印字電圧17V、パルス幅1.8msの条件で発色させ、発色画像濃度を分光測色計(SpectroeyeLT、X-rite社製)で測定した。
[Before test]
A portion of each thermal recording paper is cut out and developed using a thermal paper color test device (trade name: TH-PMH type, manufactured by Okura Electric Co., Ltd.) under the conditions of a printing voltage of 17 V and a pulse width of 1.8 ms. Was measured with a spectrocolorimeter (Spectroeye LT, manufactured by X-rite).
[耐熱性試験]
各感熱記録紙の一部を切り取り、試験前と同様にして飽和発色させた。次いで、恒温器(商品名:DK−400、YAMATO製)中で80℃、90℃、100℃の各温度で24時間保持した。試験後の光学濃度を分光測色計(SpectroeyeLT、X-rite社製)で測定した。
[Heat resistance test]
A part of each thermal recording paper was cut out and saturated color was developed in the same manner as before the test. Subsequently, it hold | maintained for 24 hours at each temperature of 80 degreeC, 90 degreeC, and 100 degreeC in a thermostat (brand name: DK-400, product made from YAMATO). The optical density after the test was measured with a spectrocolorimeter (Spectroeye LT, manufactured by X-rite).
[耐湿熱性試験]
各感熱記録紙の一部を切り取り、試験前と同様にして飽和発色させた。次いで、低温恒温恒湿器(商品名:THN050FA、ADVANTEC製)中で温度40℃、湿度90%の条件で24時間保持した。試験後の光学濃度を分光測色計(SpectroeyeLT、X-rite社製)で測定した。
[Moisture and heat resistance test]
A part of each thermal recording paper was cut out and saturated color was developed in the same manner as before the test. Subsequently, it was kept for 24 hours under conditions of a temperature of 40 ° C. and a humidity of 90% in a low temperature constant temperature and humidity chamber (trade name: THN050FA, manufactured by ADVANTEC). The optical density after the test was measured with a spectrocolorimeter (Spectroeye LT, manufactured by X-rite).
[耐可塑剤性試験]
各感熱記録紙の一部を切り取り、試験前と同様にして飽和発色させた。次いで、各試験紙の発色面及び裏面に塩化ビニルラップフィルム(可塑剤が含まれているもの)を密着させそのまま40℃で4時間保持した。試験後の発色画像濃度を分光測色計(SpectroeyeLT、X-rite社製)で測定した。
[Plasticizer resistance test]
A part of each thermal recording paper was cut out and saturated color was developed in the same manner as before the test. Next, a vinyl chloride wrap film (containing a plasticizer) was brought into close contact with the color development surface and the back surface of each test paper, and held at 40 ° C. for 4 hours. The color image density after the test was measured with a spectrocolorimeter (Spectroeye LT, manufactured by X-rite).
[耐油性試験]
各感熱記録紙の一部を切り取り、試験前と同様にして飽和発色させた。次いで、サラダオイル中に浸漬し、室温で1時間後の発色画像濃度を分光測色計(SpectroeyeLT、X-rite社製)で測定した。
[Oil resistance test]
A part of each thermal recording paper was cut out and saturated color was developed in the same manner as before the test. Subsequently, it was immersed in salad oil, and the color image density after 1 hour at room temperature was measured with a spectrocolorimeter (Spectroeye LT, manufactured by X-rite).
表2の結果から、いずれの添加剤を用いた場合も、増感剤EGPEを用いた場合に比較して画像の発色性と保存性は同等以上であり、中でも耐可塑剤性に優れており、特にビス[4−(2−ヒドロキシエトキシ)フェニル]スルホンを用いた場合には耐油性も顕著に改善されることが判明した。
From the results shown in Table 2, the color developability and storage stability of the image are equal to or higher than those using the sensitizer EGPE, and any of these additives is superior in plasticizer resistance. In particular, when bis [4- (2-hydroxyethoxy) phenyl] sulfone is used, it has been found that the oil resistance is remarkably improved.
Claims (6)
(B)下記式(I)
(式中、R1〜R3は、ハロゲン原子、ニトロ基、C1〜C6アルキル基、C1〜C6アルコキシ基、C2〜C6アルケニル基、C1〜C6ハロアルキル基、N(R4)2基(式中、R4は水素原子、フェニル基、ベンジル基、又はC1〜C6アルキル基を表す)、NHCOR5(式中、R5は、C1〜C6アルキル基を表す)、置換基を有してもよいフェニル基、又は置換基を有してもよいベンジル基を表し、n1及びn3は、それぞれ独立して、0〜5のいずれかの整数を表し、n2は、0〜4のいずれかの整数を表す)で表される化合物、
下記式(II)
(式中、R1〜R3は、式(I)におけるR1〜R3と同じものを表し、n2及びn3は、式(I)におけるn2及びn3と同じものを表し、n4は、0〜7のいずれかの整数を表す)で表される化合物、及び
下記式(III)
(式中、R1〜R3は、式(I)におけるR1〜R3と同じものを表し、n2、n3及びn4は、式(II)におけるn2、n3及びn4と同じものを表す)で表される化合物
からなる群から選ばれる少なくとも1種、及び
(C)下記式(IV)
(式中、R11及びR12は、それぞれ独立して、水素原子、C1〜C6アルキル基、C2〜C6アルケニル基、又はC1〜C6アシル基(炭素数にカルボニル基の炭素を含む。)を表し、またR11とR12とが一緒になって5員環を形成してもよい。)で表される化合物、
下記式(V)
(式中、n11及びn12は、それぞれ独立して、1〜5のいずれかの整数を表す。)で表される化合物、
下記式(VI)
(式中、R8は水素原子、C1〜C6アルキル基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表し、R9及びR10はハロゲン原子、ニトロ基、C1〜C6アルキル基、C1〜C6アルコキシ基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表し、Arは置換基を有してもよいフェニル基又は置換基を有してもよい5〜6員ヘテロアリール基を表し、n9及びn10は独立して0〜4のいずれかの整数を表す。)で表される化合物、
下記式(VII)
(式中、R6及びR7は、それぞれ独立して、C1〜C6アルキル基、C2〜C6アルケニル基、又はC1〜C6ハロアルキル基を表す。)で表される化合物、及び
下記式(VIII)
(式中、n13〜n18は、それぞれ独立して、0又は1を表す。)
で表される化合物からなる群から選ばれる少なくとも1種、
を含有することを特徴とする記録材料。 (A) at least one chromogenic dye;
(B) The following formula (I)
(Wherein R 1 to R 3 are a halogen atom, a nitro group, a C 1 to C 6 alkyl group, a C 1 to C 6 alkoxy group, a C 2 to C 6 alkenyl group, a C 1 to C 6 haloalkyl group, N (R 4 ) 2 groups (wherein R 4 represents a hydrogen atom, a phenyl group, a benzyl group, or a C 1 -C 6 alkyl group), NHCOR 5 (wherein R 5 is a C 1 -C 6 alkyl group) Represents a phenyl group that may have a substituent, or a benzyl group that may have a substituent, and n1 and n3 each independently represent an integer of 0 to 5 , N2 represents any integer of 0 to 4),
The following formula (II)
(Wherein R 1 to R 3 represent the same as R 1 to R 3 in formula (I), n2 and n3 represent the same as n2 and n3 in formula (I), and n4 represents 0 A compound represented by any one of -7, and the following formula (III)
(Wherein R 1 to R 3 represent the same as R 1 to R 3 in formula (I), and n2, n3, and n4 represent the same as n2, n3, and n4 in formula (II)). And at least one selected from the group consisting of compounds represented by formula (IV):
(Wherein R 11 and R 12 are each independently a hydrogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 1 -C 6 acyl group (the number of carbon And a compound represented by the following formula: R 11 and R 12 may be combined to form a 5-membered ring.
The following formula (V)
(Wherein, n11 and n12 each independently represents an integer of 1 to 5),
The following formula (VI)
(In the formula, R 8 represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 1 -C 6 haloalkyl group, and R 9 and R 10 represent a halogen atom, a nitro group, C 1 -C 6 alkyl group, C 1 -C 6 alkoxy group, C 2 -C 6 alkenyl group, or an C 1 -C 6 haloalkyl group, Ar is a phenyl group or a substituted group may have a substituent A 5- to 6-membered heteroaryl group which may have, n9 and n10 independently represent any integer of 0 to 4),
The following formula (VII)
(Wherein R 6 and R 7 each independently represent a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 1 -C 6 haloalkyl group), And the following formula (VIII)
(In the formula, n13 to n18 each independently represents 0 or 1.)
At least one selected from the group consisting of compounds represented by:
A recording material comprising:
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JP7345712B1 (en) * | 2022-03-31 | 2023-09-15 | 日本製紙株式会社 | heat sensitive recording material |
WO2023190315A1 (en) * | 2022-03-31 | 2023-10-05 | 日本製紙株式会社 | Heat-sensitive recording body |
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